Dimethylformamide → 2-Methyl-4-(2-methyl-benzyloxy)-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A 2.5M solution of n-BuLi (2.1 mL, 5.26 mmol) in THF was added dropwise to a −78° C. solution of 31.2 (1.46 g, 5.01 mmol) in THF (25 mL). The reaction was stirred at −78° C. for 15 minutes and then DMF (3.3 mL) was added. Cooling was removed after 5 minutes and the reaction was allowed to warm to room temperature. The reaction was partitioned between ethyl acetate and water and the aqueous layer was extracted 1 additional time with ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated. The resulting residue was purified via radial chromatography (50% ethyl acetate in hexanes0 to yield 269 mg (22%) of 2-Methyl-4-(2-methyl-benzyloxy)-benzaldehyde (31.3). LC/MSD m/e: 241.2 (M+H).

Provenance & Evidence