Diisobutylaluminum hydride → HCID 22226108, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of(E)-2-fluoro-3-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enoic acid ethyl ester (Intermediate 6, 2.2 g, 5.85 mmol) in THF (50 mL) at −78° C. was added DIBAL-H (23.4 mL, 1.0 M in CH2Cl2, 23.4 mmol) over 10 min. After stirring at −78° C. for 3 h, the reaction was quenched with aqueous NH4Cl followed by 1M HCl and was extracted with Et2O (×3). The combined organic layer was 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 (1.02 g, 45% over 2 steps).

Provenance & Evidence