Diisobutylaluminumhydride → HCID 59882242, compound

Participants

Reaction Steps

To a stirred solution of methyl (2S)-(4-chlorophenyl)(cyclopropyl)ethanoate (7.72 g, 34.4 mmol) in methylene chloride (300 ml) at −78° C. under nitrogen is added diisobutyl aluminum hydride (86 ml of a 1.0 M solution in methylene chloride, 86.0 mmol). The reaction mixture is allowed to warm to room temperature and stirred for an additional hour. The reaction is quenched by the addition of saturated aqueous ammonium chloride and then filtered. The organic layer is separated, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel eluting with ether:hexane (15:85) to afford the title compound as a colorless liquid (5.45 g, 80%) which is characterized by 1HNMR, 13CNMR and mass spectral analyses.

Provenance & Evidence