Diisobutylaluminumhydride → 3-(3-Quinolyl)-2-propen-1-ol

Participants

Reaction Conditions

Reaction Steps

The 3-(3-quinolyl)-2-propenoate (141 g, 0.621 moles) was dissolved in 2.0 L anhydrous methylene chloride in a 5-L round-bottom flask with overhead stirring and cooled to −57° C. with isopropanol/dry ice bath. Diisobutylaluminum hydride (1.55 L, 1.0 M in methylene chloride) was added in a slow stream, keeping the temperature of the reaction mixture below −40° C. After 30 minutes, the starting ester is consumed. While cooling with dry ice/acetone, 434 mL MeOH was added dropwise and the mixture was allowed to warm to room temperature. Then, 2 L of 10% sodium potassium tartrate was added portionwise to the solution and the mixture was stirred for 1 h at room temperature. The layers were separated. The organic layer was washed with 2 L aq. NaCl solution and dried over MgSO4. Evaporation gave a solid which was recrystallized from EtOAc to afford a yield of 71 g (62%) of a pinkish solid.

Provenance & Evidence