Sulfuric Acid → 3-(2,2-Dimethylpropyl)cyclobutane-1-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of N-methoxy-N-methyl-3-(2,2-dimethylpropyl)cyclobutanecarboxamide (95.2 g) in toluene (330 mL) was added diisobutylaluminum hydride (1.0M in toluene) (486 mL) dropwise at −78° C. After the mixture was stirred at −78° C. for 3 hr, 1.5 M sulfuric acid (648 mL) was added dropwise to the mixture at ice temperature. The mixture was extracted with toluene and the combined organic layer was washed with 1 M sulfuric acid, water and brine, then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate comprising the title compound was used in the next step.

Provenance & Evidence