Boron trifluoride etherate → HCID 13988265, compound

Participants

Reaction Steps

5 g (22.1 mmol) of methyl (4aS,7aS)-1-hydroxy-7-hydroxymethyl-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate was dissolved in 25 ml of methanol and catalytic amount of trifluoroboron diethylether was added thereto. The reaction mixture was stirred at room temperature for 20 hours and then the reaction was stopped by the addition of saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and distilled under vacuum. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethylacetate=5/1, v/v) to obtain 5.26 g (Yield 100%) of methyl (1R,4aS,7aS)-7-hydroxymethyl-1-methoxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate as an oil.

Provenance & Evidence