Sodium Hydroxide → HCID 22664982, compound

Participants

Reaction Steps

Under a nitrogen stream, lithium aluminum hydride (0.38 g, 0.01 mol) was suspended in dehydrating ether (8 ml) and ethyl 1-(1-hydroxy-1-phenylmethyl)cyclopentanecarboxylate (2.46 g, 0.01 mol) as 8 ml of a dehydrating ether solution was added dropwise over 30 min while stirring the mixture at room temperature. After the completion of dropwise addition, the mixture was stirred for 30 min while gently refluxing, then 10% aqueous sodium hydrogen carbonate (1 ml) was slowly added dropwise under ice-cooling. Then 20% aqueous sodium hydroxide (2 ml) was added dropwise and the ether layer was taken by decantation. The residue was washed twice with ether (10 ml). The ether layer was combined and the mixture was dehydrated over anhydrous magnesium sulfate and concentrated. The residual solution (2.01 g) was purified by silica gel column chromatography (ethyl acetate/hexane=2/3) to give the title compound (1.8 g) as a colorless oil (yield 87%).

Provenance & Evidence