Diisobutylaluminum hydride → 2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of (tert-butyl-dimethyl-silanyloxy)-cyclopropyl-acetic acid methyl ester (1.66 g, 6.79 mmol) in DCM (27 mL) at −78° C. under a nitrogen atmosphere was added DIBAL-H (20.37 mL, 20.37 mmol, 1.0M in toluene) dropwise. The reaction mixture was stirred at −78° C. for 2.5 hours then at 0° C. for 1 hour before being quenched with Rochelle's salt (30 mL, 1M aqueous solution). The mixture was extracted with ethyl acetate (3×30 mL) before the combined organic phases were dried (Na2SO4) and concentrated in vacuo giving 2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethanol as a pale orange oil (764 mg, 52%). 1H NMR (400 MHz, CDCl3): δ 3.66-3.49 (2H, m), 3.09 (1H, ddd, J=7.96, 6.40, 3.80 Hz), 1.96 (1H, dd, J=7.43, 5.46 Hz), 0.91 (9H, s), 0.91-0.82 (1H, m), 0.57-0.43 (2H, m), 0.34-0.24 (1H, m), 0.23-0.14 (1H, m), 0.11 (3H, s), 0.07 (3H, s).

Provenance & Evidence