Diisobutylaluminumhydride → HCID 22493865, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6,6,9,9-tetramethyl-4-trifluoromethyl-6,7,8,9-tetrahydro-benzo[g]chromen-2-one (Intermediate 3, 348 mg, 1.07 mmol) in CH2Cl2 (5 mL) at −78° C. was added di-iso-butyl aluminum hydride (DIBAL-H, 1.40 mL, 1.0 M in CH2Cl2) over 10 min. After stirring at −78° C. for 3 h, the reaction was quenched with aqueous NH4Cl, followed by 1M HCl, and the aqueous layer was extracted with Et2O (×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10% EtOAc-hexane) to give the title compound as a clear oil (346 mg, 99%) that was used directly in the next reaction.

Provenance & Evidence