Metal-Free Oxidative Cleavage of C-C bond in α-hydroxy-βoxophosphonates
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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 25 Supporting Information Metal-Free xidative Cleavage of C-C bond in α-hydroxy-βoxophosphonates Ahmed Satyanarayana Battula, Atul Kumar, Qazi Naveed Medicinal Chemistry Division, IIIM, Jammu, Jammu and Kashmir, 8, India. Academy of Scientific and Innovative Research (AcSIR), CRRI P.., New Delhi-25, India.
2 Contents with page no.: S.No. Contents Page no.. General information 3 2. Experimental procedures 3 3. Spectral data of acid compounds 4 4. References 7 5. H, 3 C-NMR spectra 8 2
3 . General Information. All chemicals were obtained from Sigma-Aldrich Company and used as received. H and 3 C NMR spectra were recorded on Brucker-Avance DPX FT-NMR and MHz instruments. Chemical shifts of protons reported in parts per million (ppm) downfield from tetramethylsilane and are referenced to the residual proton in the NMR solvents (CDCl3: 7.26 ppm). 3 C-NMR spectra were recorded at 25 MHz or MHz: chemical data for carbons are reported in parts per million (ppm, δ scale) down field from tetra methyl silane and are referenced to the carbon resonance of the solvent (CDCl3:7 ppm). Mass spectra of compounds were recorded with ESI-MS. 2. Experimental procedures Synthesis of α-hydroxy-β-oxo phosphonates (HP). α-hydroxy-β-oxo phosphonates were synthesized by the standard reported protocol. Synthesis of Diethyl (2-oxo-2-phenylethyl)phosphonate (4). 2 Diethyl (2-oxo-2-phenylethyl)phosphonate (4) was synthesized by the reported protocol Procedure for oxidative C-C bond cleavage in HP to acids. Reaction vessel charged with mmol of α-hydroxy-β-oxo phosphonate and was added 2 ml of toluene, 2 mmol of TBHP. The reaction mixture allowed stirring for 4 days at room temperature. After completion of the reaction, crude mass was extracted with ethyl acetate. Then it was purified by column chromatography using silica gel (# -2 mesh size) and eluted with ethyl acetate and hexane (:4) to produced desire product 2 in good yields (68-95 %). 3
4 3. Spectral data of acid compounds. Benzoicacid (2a). 3 H NMR ( MHz, MeD) δ 3 (d, J = 7.6 Hz, 2H), 4 (t, J = 7.3 Hz, H), 7.43 (t, J = 7.6 Hz, 2H); 3 C NMR ( MHz, MeD) δ 76, 34., 3.86,.8, 29.; ESI-MS: 45. (M + + Na). 4-Fluorobenzoicacid (2b). 4 F H NMR ( MHz, CDCl 3 ) δ 8.4 (dd, J = 8.2, 5.8 Hz, 2H), 7.5 (t, J = Hz, 2H); 3 C NMR ( MHz, MeD) δ 68.77, 68.45, 65.94, 33, 33.43, 28.42,, 6.29; ESI-MS: 39. (M + -). 4-Chlorobenzoicacid (2c). 4 Cl H NMR ( MHz, CDCl3) δ 4 (d, J = 8.6 Hz, 2H), 7.46 (d, J = 8.6 Hz, 2H); 3 C NMR ( MHz, MeD) δ 68.76,.29, 32.35,.73, 29.76; ESI-MS: 55.2 (M + -). 4-Bromobenzoicacid (2d). 3 Br H NMR ( MHz, MeD) δ 7.82 (d, J = Hz, 2H), 5 (d, J = Hz, 2H); 3 C NMR (26 MHz, MeD) δ 68.89, 32.84,, 3.5, 28.8; ESI-MS: 99.2 (M + -). 3-Nitrobenzoicacid (2e). 3 N 2 H NMR ( MHz, CDCl 3 ) δ 8.97 (s, H), (m, 2H), 7.73 (t, J = Hz, H); 3 C NMR (26 MHz, MeD) δ 65.95, 48.25, 32, 32.47, 29.67, 26.89, 23.89; ESI-MS: 66. (M + -). 4
5 4-Nitrobenzoicacid (2f). 3 N 2 H NMR ( MHz, MeD) δ 8.23 (d, J = 8.8 Hz, 2H), 8.3 (d, J = 8.8 Hz, 2H); 3 C NMR (26 MHz, MeD) δ 67.63, 5.96, 37.63, 3.97, 27; ESI-MS: 66.2 (M + -). 4-Methylbenzoicacid (2g). 3 H NMR ( MHz, CDCl 3 ) δ (d, J = 8.2 Hz, 2H), 7.28 (d, J = Hz, 2H), 2.43 (s, 3H); 3 C NMR ( MHz, CDCl 3 ) δ 72.22, 44.64,.27, 29.22, 26., 2.76; ESI-MS: 37.4 (M + + ). 3,4-Dimethylbenzoicacid (2h). 5 H NMR ( MHz, CDCl 3 ) δ 7.88 (s, H), 7.85 (d, J = 7.8 Hz, H), 7.23 (d, J = 7.8 Hz, H), 2.33 (s, 3H), 2.32 (s, 3H); 3 C NMR (26 MHz, CDCl 3 ) δ 77, 43.4, 36.92, 3.22, 29.8, 27.87, 26.85, 2.8, 9.74; ESI-MS: 48.8 (M + -). 4-Methoxybenzoicacid (2i). 3 H NMR ( MHz, MeD) δ 7.87 (d, J = 8.9 Hz, 2H), 6.87 (d, J = 8.9 Hz, 2H), 3.75 (s, 3H); 3 C NMR (26 MHz, MeD) δ 69.83, 69, 32.85, 2, 4.69, 55.98; ESI-MS: 5.2 (M + -). 4-Methoxy-2-methylbenzoic acid (2j). 6 5
6 H NMR ( MHz, DMS) δ 7.84 (d, J = 8.3 Hz, H), 6.84 (s, H), 6.82 (d, J = 2.4 Hz, H), 3.82 (s, 3H), 2 (s, 3H); 3 C NMR (26 MHz, DMS) δ, 6.7, 42.5, 32.78, 22, 6.69,., 55.22, 2.86; ESI-MS: 67. (M + +). 2,4-Dichlorobenzoic acid (2k). 4 Cl Cl H NMR ( MHz, CDCl 3 ) δ 7.99 (d, J = Hz, H), 3 (d, J =.9 Hz, H), 7.35 (dd, J =, Hz, H); 3 C NMR ( MHz, CDCl 3 ) δ 69.27, 39.56, 3,, 3.46, 27.8, 26.64; ESI-MS: 89.2 (M + -). 3-Bromo-4-Fluorobenzoicacid (2l). 7 F Br H NMR ( MHz, CDCl 3 ) δ 8.34 (dd, J = 6.6, 2. Hz, H), 7 (ddd, J = 8.6, 4.7, 2. Hz, H), 7.23 (dd, J =, 8. Hz, H); 3 C NMR ( MHz, CDCl 3 ) δ.2, 63.97, 6.43, 36., 39, 35, 3.46, 26.77, 26.73, 6.82, 9, 9.68, 9.47; ESI-MS: 26.8 (M + -). 4-Hydroxybenzoic acid (2m). 8 H H NMR ( MHz, DMS) δ.28 (s, H), 7.8 (d, J = 8.7 Hz, 2H), 6.83 (d, J = 8.7 Hz, 2H); 3 C NMR ( MHz, DMS) δ 67.66, 65, 3, 2.79, 9; ESI-MS: 3 (M + -). 5-Methylthiophene-2-carboxylic acid (2n). 9 S H H NMR ( MHz, CDCl 3 ) δ 7.7 (d, J = 3.6 Hz, H), 6.8 (d, J = 3. Hz, H), 6 (s, 3H); 3 C NMR (26 MHz, CDCl 3 ) δ 65.6, 47.76, 33.4, 2, 24.63, 3.78; ESI-MS: 4 (M + -). 6
7 Benzofuran-2-carboxylic acid (2o). 9 H H NMR ( MHz, MeD) δ 7.72 (d, J = 7.9 Hz, H), 7 (t, J = 4.2 Hz, 2H), 7.43 (m, H), 7.3 (t, J = Hz, H); 3 C NMR (26 MHz, MeD) δ 69, 55.74, 42, 27.33, 27., 2, 22.64, 3.45, 6; ESI-MS: 63. (M + +). Diethyl (2-oxo-2-phenylethyl)phosphonate (4) 2 P H NMR ( MHz, CDCl 3 ) δ (m, 2H), (m, H), (m, 2H), (m, 4H), 3.64 (d, J = 22.7 Hz, 2H),.28 (t, J = 7. Hz, 6H); ESI-MS: 25 (M + +). 4. References:. Battula, S.; Battini, N.; Singh, D.; Ahmed, Q. N. rg. Biomol. Chem. 25, DI:.39/c5obk. 2. Yi, N.; Wang, R.; Zou, H.; He, W.; Fu, W.; He, W., J. rg. Chem. 25, 8, Shaikh, T. M.; Honga, F. E. Adv. Synth. Catal. 2, 353, Shaikh, T. M.; Arumugam, S. Eur. J. rg. Chem. 28, Nemoto, K.; Yoshida, H.; Egusa, N.; Morohashi, N.; Hattori, T. J. rg. Chem. 2, 75, Nguyen, T.-H.; Chau, N. T. T.; Castanet, A.-S.; Nguyen, K. P. P.; Mortier, J. J. rg. Chem. 27, 72, Kumar, S.; Dixit, S. K.; Awasthi, S. K. Tetrahedron Lett. 24, 55, Silveira-Dorta, G.; Monzón, D. M.; Crisóstomo, F. P.; Martín, T.; Martína, V. S.; Carrillo, R., Chem. Commun. 25, 5, Kumar, K. A. A.; Venkateswarlu, V.; Vishwakarma, R. A.; Sawant, S. D., Synthesis 25, 47, A H. 7
8 5. NMR spectra of products (2a-2l) 2a. Benzoic acid
9 9 2b. 4-Fluorobenzoic acid F F
10 2c. 4-Chlorobenzoic acid Cl Cl
11 2d. 4-Bromobenzoic acid Br Br
12 2 2e. 3-Nitrobenzoic acid N 2 N 2
13 2f. 4-Nitrobenzoic acid N N
14 4 2g. 4-Methylbenzoic acid
15 5 2h. 3,4-Dimethylbenzoic acid
16 6 2i. 4-Methoxybenzoic acid
17 7 2j. 4-Methoxy-2-methylbenzoic acid
18 8 2k. 2,4-Dichlorobenzoic acid Cl Cl Cl Cl
19 9 2l. 3-Bromo-4-Fluorobenzoicacid F Br F Br
20 2 2m. 4-Hydroxybenzoic acid H H
21 2 2n. 5-Methylthiophene-2-carboxylic acid S H S H
22 22 2o. Benzofuran-2-carboxylic acid H H
23 23 Diethyl (2-oxo-2-phenylethyl)phosphonate (4) P
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