Aluminium lithium hydride → 2-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetic acid (140 mg, 0.414 mmol) and LAH (0.414 mL, 0.414 mmol) in THF (5 mL) was stirred at 0° C. for 2 h. The reaction was quenched with water (1 mL) dropwise and then stirred at rt for 10 min. The mixture was diluted with EtOAc (5 mL) and filtered. The filtrate was washed with water, dried with MgSO4, filtered, and concentrated in vacuo to afford the title compound (64 mg, 48% yield) as a clear oil. LCMS, [M+Na]+=347.1. 1H NMR (500 MHz, CDCl3) δ 7.29-7.16 (m, 3H), 7.10-6.96 (m, 3H), 6.96-6.87 (m, 2H), 6.76 (ddd, J=8.1, 2.5, 1.0 Hz, 1H), 3.77 (s, 2H), 3.62 (t, J=7.3 Hz, 2H), 2.07-1.88 (m, 4H), 1.73-1.57 (m, 4H), 1.38 (t, J=7.3 Hz, 2H).

Provenance & Evidence