Red-Al → HCID 69322475, compound

Participants

Reaction Conditions

Reaction Steps

A 1-L reaction flask equipped with a stirrer, a thermometer, a reflux condenser, a heating mantle, and an addition funnel was charged with Vitride (300 g, 1.32 mol) and toluene (300 g). The resulting mixture was stirred at 20° C. The Diels-Alder product containing 1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-2-methyl-cyclohex-3-enecarbaldehyde (300 g, 0.97 mol, synthesized as above in EXAMPLE VIII) was added over about 2 hours. The temperature was allowed to rise to 43° C. The reaction mass was aged for 3 hours. The excessive Vitride reagent was quenched with ethyl acetate (100 g), followed by sodium hydroxide (25%, 800 g). The temperature was allowed to rise to 50° C. and stirred for another 0.5 hours. The organic phase was washed with hot water (1 L) twice and concentrated to yield the crude product [1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-2-methyl-cyclohex-3-enyl]-methanol (295 g).

Provenance & Evidence