Water → HCID 14986505, compound

Participants

Reaction Steps

6-Acetoxy-2-acetyl-5,6-dihydro-5,5-dimethyl-7-(4-nitrobenzamido)-7H-thienopyran (0.60 g, 1.39 mmol) was treated with aqueous sodium hydroxide (1N, 1.5 mL, 1.5 mmol) in methanol (10 mL) at rt and stirred for 2 h. The resultant solution was poured into water and extracted with 5% isopropanol in dichloromethane. The organic phase was washed with water (3×) and dried over magnesium sulfate. The solvent was evaporated in vacuo and the resultant solid triturated in diethyl ether to give the product, 0.36 g (66%), as a pale yellow solid: mp 223°-225° C.; IR (KBr) 1647, 1601, 1530 and 1458 cm-1 ; MS: m/z 391 (MH+); 1H NMR (DMSO-d6): δ 1.23 (s, 3H), 1.42 (s, 3H), 2.45 (s, 3H), 3.84 (m, 1H, simplifies to d, J=8.9 Hz with D2O), 5.01 (m, 1H, simplifies to d, J=8.9 Hz, with D2O), 5.86 (d, J=5.9 Hz, 1H, exchanges with D2O), 7.47 (s, 1H), 8.14 (d, J=8.8 Hz, 2H), 8.36 (d, J=8.8 Hz, 2H) and 9.27 (d, 1H, exchanges with D2O).

Provenance & Evidence