Diisobutylaluminum hydride → HCID 11733716, compound

Participants

Reaction Conditions

Reaction Steps

DIBAL (1.0 M in hexane, 2.1 mL, 2.1 mmol) was added dropwise to a solution of the acetal 35 (329 mg, 0.67 mmol) in dry CH2Cl2 (6.7 mL) at 0° C. After stirring for 2 h, the reaction was quenched with saturated aqueous sodium tartrate (20 mL) followed by vigorously stirring for several hours. The aqueous phase was extracted with CH2Cl2 (3×10 mL) and the combined organic layers were washed with brine (10 mL). The residue obtained after drying over MgSO4 and evaporation under vacuum was dissolved in anhydrous CH2Cl2 (6 mL) and DMSO (12 mL), treated with N,N-diisopropylethylamine (0.52 mL, 3 mmol), cooled to 0° C. and treated with pyridinium sulfur trioxide (477 mg, 3 mmol). The reaction mixture was stirred at ambient temperature for 1 h, diluted with ethyl ether (50 mL) and washed with aqueous HCl (0.5 N, 50 mL) and brine (10 ml). The separated organic layer was dried over MgSO4. Filtration and concentration followed by short flash column chromatography (hexane/EtOAc 4:1) provided the crude aldehyde 37 (270 mg, 0.55 mmol) as a colorless oil which was used without further purification.

Provenance & Evidence