Benzyl Alcohol → HCID 53761132, compound

Participants

Reaction Conditions

Reaction Steps

1.13 g (5.0 mmol) of methyl (4aS,7aS)-1-hydroxy-7-hydroxymethyl-1,4a,5, 7a-tetrahydrocyclopenta[c]pyran-4-carboxylate was dissoved in 10 ml of dried tetrahydrofuran, then 2.60 ml (25 mmol) of benzyl alcohol and catalytic amount of trifluoroboron diethylether were added thereto. The resulting mixture was stirred while refluxing for 48 hours at 75° C. The mixture was cooled down to room temperature and concentrated. The residue was dissolved in ethylacetate and then washed with saturated aqueous sodium bicarbonate solution and saturated saline solution The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexanelethylacetate=2/1, v/v) to obtain 0.61 g (Yield 39%) of methyl (1R,4aS,7aS)-1-benzyloxy-7-hydroxymethyl-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate as an oil.

Provenance & Evidence