Diisobutylaluminum hydride → HCID 11081513, compound

Participants

Reaction Steps

DIBAL (1.0 M in hexane, 2.1 mL, 2.1 mmol) was added dropwise to a solution of the acetal 36 (329 mg, 0.67 mmol) in dry CH2Cl2 (6.7 mL) at 0° C. After the mixture was stirred for 2 h, the reaction was quenched with saturated aqueous sodium tartrate (20 mL) followed by vigorous 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). After drying over MgSO4 and evaporation under vacuum, the residue was used for the next reaction without further purification. The crude alcohol in CH2Cl2 (13 mL) was treated with Dess-Martin periodinane (340.8 mg, 0.80 mmol). After the reaction was complete, the mixture was quenched with saturated NaHCO3 (20 mL). The aqueous layer was extracted with CH2Cl2 (2×10 mL) and the combined extracts were dried over anhydrous MgSO4. Filtration and concentration followed by short flash column chromatography filtration (hexane/EtOAc 9:1) provided crude aldehyde 38 (267 mg, 81%) as a colorless oil which was used without further purification.

Provenance & Evidence