Diisobutylaluminum hydride → HCID 11789327, compound

Participants

Reaction Conditions

Reaction Steps

(S)-N-methoxy-N,2,2,4-tetramethyl-1,3-dioxolane-4-carboxamide (23.1 g, 114 mmol) was dissolved in THF (600 mL) and cooled to −78° C. DIBAL-H (1M in toluene, 125 ml, 125 mmol) was added slowly through an addition funnel over about 15 minutes. The reaction was stirred for an additional 30 minutes at −78° C. and then quenched with saturated aqueous NH4Cl. The mixture was partitioned between EtOAc and water. The two layers were filtered through a silica plug and separated. The organic layer was dried over sodium sulfate, filtered and concentrated to afford (S)-2,2,4-trimethyl-1,3-dioxolane-4-carbaldehyde (16.4 g, 114 mmol, 100% yield).

Provenance & Evidence