Diisobutylaluminum hydride → HCID 90409078, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of 2-(1-(2-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetaldehyde (150 mg, 0.465 mmol) in DCM (5 mL) under N2 was added dropwise DIBAL-H (0.558 mL of a 1 M solution in DCM, 0.558 mmol). The reaction mixture was stirred at −78° C. for 2 h, after which CELITE® (3500 mg) was added. The reaction was then quenched at −78° C. with sat. aq. NH4Cl (2 mL). The mixture was stirred at rt for 30 min, after which MgSO4 (1000 mg) was added. Stirring was continued at rt for 1 h, after which the mixture was filtered. The solid was washed with DCM (4×). The combined filtrates were concentrated in vacuo to give a crude oil, which was purified by flash chromatography (SiO2) using a gradient from 0% to 50% EtOAc/hexane (10 min) to give the title compound (135 mg, 0.416 mmol, 89% yield) as a clear oil. 1H NMR (CDCl3) δ: 7.78-7.73 (dd, J=7.9, 1.9 Hz, 1H), 7.38-7.32 (m, 2H), 7.20-7.07 (m, 3H), 7.01-6.95 (m, 2H), 6.83-6.78 (dd, J=8.0, 1.4 Hz, 1H), 3.96-3.84 (s, 2H), 3.75-3.66 (t, J=7.4 Hz, 2H), 2.61-2.50 (m, 2H), 1.98-1.88 (m, 2H), 1.75-1.61 (m, 4H), 1.51-1.42 (t, J=7.4 Hz, 2H), 1.33 (s, 1H).

Provenance & Evidence