Water → HCID 14986498, compound

Participants

Reaction Steps

Aqueous sodium hydroxide (50%, 0.15 g, 1.87 mmol) was added to a solution of 6-acetoxy-2-acetyl-5,6-dihydro-5,5-dimethyl-7-(2-oxopyrrolidin-1-yl)-7H-thieno[3,2-b]pyran (0.45 g, 1.28 mmol) in methanol (20 mL) and stirred at rt for 1 h. The solution was poured into water (100 mL) and extracted into dichloromethane. The dichloromethane solution was washed with water (3×) and dried over magnesium sulfate. The solvent was evaporated in vacuo and the resultant oil was crystallized from diethyl ether and hexanes to give the product, 0.327 g (83%), as a colorless solid: mp 102°-106° C.; IR (KBr): 1665 and 1561 cm-1 ; MS: m/z 310 (MH+); 1H NMR (CDCl3): δ1.31(s, 3H), 1.51(s, 3H), 2.07(m, 2H), 2.48(s, 3H), 2.51(m, 2H), 3.34(m, 2H), 3.45(d, J=6.2 Hz, 1H, exchanges with D2O), 3.80(dd, J=6.2 Hz and J=9.4 Hz, 1H, simplifies to d, J=9.4 Hz, with D2O), 5.29(d, J=9.4 Hz, 1H) and 7.14(s, 1H).

Provenance & Evidence