Methanol → 4-Methyl-3-phenylpentanal

Participants

Reaction Steps

Under a nitrogen atmosphere, N-methyl-N-methoxy-4-methyl-3-phenyl-pentaneamide (215 mg) was dissolved in tetrahydrofuran (9.1 mL) at −78° C., and a diisobutylaluminum hydride/toluene solution (1.5 M, 1.2 mL) was added. After one hour, methanol (3 mL) was added to the reaction system, the temperature of the mixture was returned to room temperature after termination of foaming, and the mixture was continuously stirred. The organic layer was separated by adding diethyl ether, water and a 1N aqueous hydrochloric acid thereto. The resulting organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. After filtering off the drying agent, the mixture was evaporated, to give the title compound as a colorless oil (200 mg). The resulting compound was used for the next reaction without purification.

Provenance & Evidence