Sodium Hydroxide → HCID 13676044, compound

Participants

Reaction Steps

Under a nitrogen stream, lithium aluminum hydride (4.55 g, 0.12 mol) was suspended in dehydrated ether (120 ml) and a solution (50 ml) of ethyl 1-benzoylcyclopropanecarboxylate (21.83 g, 0.1 mol) in dehydrated ether was added dropwise over 50 min while stirring under ice-cooling. The mixture was stirred at room temperature for 1.5 h, and 10% aqueous sodium hydrogen carbonate (15 ml) was slowly added dropwise under ice-cooling. Then 20% aqueous sodium hydroxide (30 ml) was added dropwise, and the mixture was stirred for 30 min. The ether layer was separated by decantation and the residue was washed twice with 30 ml of ether. The ether layer was combined, washed with saturated brine, dehydrated over anhydrous magnesium sulfate and concentrated. The residual solution (16.9 g) was purified by silica gel column chromatography (chloroform/methanol=20/1) to give the title compound (14.51 g) as a colorless oil (yield 81%).

Provenance & Evidence