Diisobutylaluminum hydride → 304004-77-1

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(tert-butyldimethylsilyloxy)-2-methylpropanoate (1.00 g, 4.30 mmol) in hexanes (15 mL) at about −78° C. was added DIBAL-H (1.0 M in hexanes, 9.47 mL, 9.47 mmol) drop-wise over about 5 min. The solution was stirred at about −78° C. for about 5 min and the cooling bath was removed. The solution was warmed to ambient temperature and stirred for about 1 h. The reaction was then re-cooled to about 0° C. and was quenched with the slow addition of a saturated solution of sodium potassium tartrate (about 20 mL). The thick suspension was stirred at ambient temperature for about 2 h until the two layers were clear. The layers were separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic extracts were washed with water and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give as the title compound (0.73 g, 83%) as a colorless oil: 1H NMR (CDCl3) δ 3.32 (s, 2H), 1.24 (s, 6H), 0.88 (d, J=2.9, 9H), 0.12 (d, J=3.2, 6H).

Provenance & Evidence