Dichloromethane → Benzyl 3-formyl-2-methylphenylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 3-cyano-2-methylphenylcarbamate (6.41 g, 24.07 mmol) in tetrahydrofuran (250 mL) at −78° C. was added DIBAL-H in dichloromethane (96 mL, 96 mmol) over 1 hr. The mixture was stirred at −78° C. for 45 min and then at room temperature for 5 hr. It was poured into ice cold water (300 mL) and the resulting mixture was stirred at room temperature for 30 min. The mixture was filtered through CELITE®, and the filtrate was concentrated to remove most of the THF. The remaining aqueous solution was extracted with ethyl acetate (4×150 mL). The combined extract was dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (5.65 g, 20.98 mmol, 87% yield) as a pale yellow solid.

Provenance & Evidence