Water → HCID 54447813, compound

Participants

Reaction Conditions

Reaction Steps

Dissolved methyl 3-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-propenoate (6.00 g, 0.0188 mol) in 80 mL of dry THF. Cooled to 0° C. under a nitrogen atmosphere, and added lithium aluminum hydride (18.8 mL of 1.0M in THF, 0.018 mol) via syringe. Warmed slowly to room temperature and stirred for 20 hours. Recooled to 0° C., and carefully added 0.8 mL water, 0.8 mL of 1N NaOH, and then 2.5 mL of water in sequence. Stirred at room temperature for 1 hour, and filtered through celite. Washed filtrate with saturated NH4Cl, dried with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 1:4 ethyl acetate:hexane then 1:2 ethyl acetate:hexane. Combined appropriate fractions, and evaporated to give 4.87 g (89% yield) of 3-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-prop-2-en-1-ol as a colorless oil.

Provenance & Evidence