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Synlett 2014; 25(09): 1331-1334
DOI: 10.1055/s-0033-1341085
DOI: 10.1055/s-0033-1341085
letter
Phospha-Michael Addition to In Situ Prepared 5-Arylmethylidene Meldrum’s Acids
Further Information
Publication History
Received: 28 February 2014
Accepted after revision: 12 March 2014
Publication Date:
08 May 2014 (online)
Abstract
Knoevenagel condensation reaction of an aldehyde and Meldrum’s acid produces a 5-arylmethylidene Meldrum’s acid, which undergoes Michael addition of a trialkyl phosphite under solvent-free conditions to afford the title compounds in good yields.
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References and Notes
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- 17 General Procedure for the Preparation of Compounds 4 and 5, Exemplified on 4a and 5a: A mixture of benzaldehyde (2 mmol), Meldrum’s acid (1 mmol), and trimethyl phosphite (2 mmol) was stirred at ambient temperature for 8 h. Progress of the reaction was monitored by TLC. After completion of the reaction, the products were purified by column chromatography using n-hexane–EtOAc (2:1) as eluent. The solvent was removed and the products were obtained. Dimethyl 2-[(Dimethoxyphosphoryl)phenylmethyl]-malonate (4a): yield: 0.149 g (45%); white powder; mp 80–81 °C. IR (KBr): 1735 (C=O), 1498, 1440, 1312, 1244, 1212, 1161, 1046, 1014 (PO), 916, 856, 829, 728 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 3.38 (s, 3 H, CO2CH3), 3.44 (d, 3 J PH = 10.7 Hz, 3 H, POCH3), 3.64 (d, 3 J PH = 10.9 Hz, 3 H, POCH3), 3.78 (s, 3 H, CO2CH3), 3.97 (dd, 3 J HH = 11.8 Hz, 2 J PH = 20.4 Hz, 1 H, PCHCH), 4.20 (dd, 3 J HH = 11.8 Hz, 3 J PH = 10.2 Hz, 1 H, PCHCH), 7.21–7.34 (m, 5 H, 5 × CH). 13C NMR (125.8 MHz, CDCl3): δ = 43.7 (d, 1 J PC = 139.2 Hz, PCH), 52.6 (CO2 Me), 52.9 (d, 2 J PC = 7.0 Hz, POMe), 53.0 (CO2 Me), 53.1 (PCHCH), 53.8 (d, 2 J PC = 6.5 Hz, POMe), 127.9, 128.6 (2 × CH), 129.6 (d, 3 J PC = 5.9 Hz, CH), 133.2 (d, 2 J PC = 7.0 Hz, C), 166.9 (d, 3 J PC = 21.2 Hz, C=O), 167.6 (C=O). 31P NMR (202.5 MHz, CDCl3): δ = 26.67 (P=O). MS (EI): m/z (%) = 330 (40) [M+], 299 (13), 271 (91), 266 (34), 239 (100), 211 (16), 189 (36), 177 (6), 161 (16), 149 (22), 131 (55), 121 (70), 109 (25), 103 (36), 93 (16), 77 (20), 59 (11). Anal. Calcd for C14H19O7P (330.27): C, 50.91; H, 5.80. Found: C, 50.7; H, 5.9. Diethyl 2-[(Diethoxyphosphoryl)(4-fluorophenyl)-methyl]malonate (4i): yield: 0.174 g (43%); colorless liquid. IR (KBr): 1740, 1735 (C=O), 1604, 1510, 1447, 1369, 1300, 1226, 1161, 1099, 1019 (PO), 962, 849, 794 cm–1. 1H NMR (500.1 MHz, CDCl3): δ = 0.93 (t, J = 7.1 Hz, 3 H, CH2CH 3), 1.12 (t, J = 7.0 Hz, 3 H, CH2CH 3), 1.22, 1.30 (2 × t, J = 7.1 Hz, 6 H, 2 × CH2CH 3), 3.75–4.05 (m, 7 H, 3 × CH 2CH3, PCHCH), 4.13 (dd, 3 J HH = 11.3 Hz, 3 J PH = 11.1 Hz, 1 H, PCHCH), 4.16 (q, J = 7.1 Hz, 2 H, CO2CH 2CH3), 6.98 (dd, 3 J HH = 8.0 Hz, 3 J FH = 8.5 Hz, 2 H, 2 × CH), 7.30–7.36 (m, 2 H, 2 × CH). 13C NMR (128.5 MHz, CDCl3): δ = 13.6, 14.0 (2 × CO2CH2 CH3), 16.2 (d, 3 J PC = 5.8 Hz, POCH2 CH3), 16.3 (d, 3 J PC = 6.2 Hz, POCH2 CH3), 43.1 (d, 1 J PC = 140.0 Hz, PCH), 53.5 (PCHCH), 61.7, 62.0 (2 × CO2 CH2CH3), 62.4 (d, 2 J PC = 6.9 Hz, POCH2), 63.1 (d, 2 J PC = 6.7 Hz, POCH2), 115.3 (d, 2 J FC = 21.3 Hz, CH), 129.5 (dd, 2 J PC = 7.1 Hz, 4 J FC = 2.7 Hz, C), 131.5 (dd, 3 J FC = 7.7 Hz, 3 J PC = 6.3 Hz, CH), 162.3 (d, 1 J FC = 250.3 Hz, CF), 166.5 (d, 3 J PC = 20.0 Hz, C=O), 167.1 (C=O). 31P NMR (202.5 MHz, CDCl3): δ = 24.25 (P=O). MS (EI): m/z (%) = 404 (38) [M+], 359 (20), 339 (11), 331 (100), 312 (28), 293 (16), 285 (91), 265 (28), 257 (43), 247 (16), 229 (67), 219 (43), 201 (13), 191 (15), 179 (34), 149 (94), 121 (32), 109 (31), 101 (21), 91 (9), 83 (38), 65 (8), 55 (13). Anal. Calcd for C18H26FO7P (404.37): C, 53.47; H, 6.48. Found: C, 53.5; H, 6.3.
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