5,5-Dimethyl-1,3-dioxane-2-propionaldehyde → 3-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a cold solution of 5,5-dimethyl-1,3-dioxane-2-propanal (2 g, 11.62 mmol) (Step 2) at -70° C. in THF (50 ml), 4-fluorophenyl magnesium bromide (8.7 ml, 2M solution in ether, 17.44 mmol) was added. After stirring at -70° C. for 2 hours, the mixture was warmed to room temperature and stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic fractions were combined and washed successively with water and brine. After drying (MgSO4), filtration and concentration, the crude compound (3.5 g) was purified by chromatography to give 3-(5,5-dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-ol (2.73 g) as a white solid: mp (DSC) 84° C. Anal Calc'd. for C15H21FO3 : C, 67.14; H, 7.89. Found: C, 67.18; H, 7.98.

Provenance & Evidence