HCID 86700848, compound → HCID 86700849, compound

Participants

Reaction Steps

An oven-dried flask under nitrogen was charged with 4-(4-chloro-phenyl)-cyclohex-3-ene-1,1-dicarboxylic acid diethyl ester (6.5 g, 19.30 mmol) in tetrahydrofuran (80 ml), and at −78° C. was added lithium alumina hydride (30.9 ml, 30.9 mmol) in one portion. The mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction was quenched with saturated aqueous sodium chloride solution (5 ml) at 0° C. The mixture was filtered and the filtrate was extracted with ethyl acetate (3×100 ml), and the residue solid was washed with acetone (100 ml). The organic solvents were combined, dried over Na2SO4, and concentrated. The residue was purified by chromatography (heptanes/acetone 1/2) to afford [4-(4-chloro-phenyl)-1-hydroxymethyl-cyclohex-3-enyl]-methanol (4.7 g, 96%) as white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.64-1.74 (m, 2H) 2.04 (d, J=3.66 Hz, 2H) 2.37-2.46 (m, 2H) 3.50 (td, J=10.80, 8.80 Hz, 4H) 6.03-6.11 (m, 1H) 7.27 (d, J=8.40 Hz, 2H) 7.36 (d, J=8.40 Hz, 2H).

Provenance & Evidence