Methanol → HCID 10042817, compound

Participants

Reaction Steps

A solution of trans-2-bromo-5,6-dihydro-6-hydroxy-5,5-dimethyl -7-(2-oxopiperidin-1-yl)-7H-thieno[3,2-b]pyran (1.35 g, 3.75 mmol), triethylamine (0.87 mL, 6.25 mmol) and bis(triphenylphosphine)-palladium(II) chloride (80 mg, 0.11 mmol) in methanol (120 mL) was heated in a stainless steel Parr pressure reactor pressurized with carbon monoxide (160 psi) at 100° C. for four days. The resultant solution was poured into water and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo. The product was purified by flash chromatography using 2% methanol in dichloromethane as the eluant to give the product, 0.83 g (65%) as a colorless solid: mp 104°-106° C.; IR(KBr): 1718, 1618 and 1565 cm-1 ; MS: m/z 340MH+); 1H NMR(CDCl3): δ 1.29 (s, 3H), 1.49 (s, 3H), 1.43 (m, 4H), 2.53 (m, 2H), 3.14 (m, 1H), 3.23 (m, 1H), 3.52 (d, J=5.4 Hz, 1H, exchanges with D2O), 3.81 (d,d, J=5.4 Hz, J=9.5 Hz, 1H, simplifies to d, J=9.5 Hz, with D2O), 3.86 (s, 3H), 5.87 (d, J=9.5 Hz, 1H) and 7.24 (s, 1H).

Provenance & Evidence