Toluene → 5-(2,2-Dimethyl-propyl)-isoxazole-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2,2-dimethyl-propyl)-isoxazole-3-carbonitrile (821 mg, 5 mmol) in Et2O (15 mL) and n-hexane (50 mL) was added dropwise at −78° C. an 1.7M toluene solution of DIBAL (11.8 mL, 20 mmol) keeping the temperature below −70° C. The mixture was stirred at −78° C. for 1 h. The reaction was quenched with EtOAc (7.5 mL), allowed to warm to 0° C., then sat. NH4Cl solution (25 mL) and 1M HCl (50 mL) were added and the mixture stirred at room temperature for 2 h. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography on silica gel (cyclohexane to cyclohexane-EtOAc 80:20) to furnish title compound as a colorless oil: TLC (cyclohexane-EtOAc 80:20) Rf=0.44; ESIMS [M+H]+=168; 1H NMR (400 MHz, DMSO-d6): δ 10.06 (s, 1H), 6.66 (s, 1H), 2.74 (s, 2H), 0.92 (s, 9H).

Provenance & Evidence