(4-Oxocyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate) → (4-Hydroxy-4-(3-methoxyphenyl)cyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-oxocyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate) (417 mg, 0.894 mmol) in THF (5 mL) at 0° C. was added 3-methoxyphenylmagnesium bromide (1.073 mL, 1.073 mmol) dropwise over a period of 5 min. The reaction was stirred at 0° C. for 2 h and quenched with sat′d aqueous NH4Cl (1 mL). The mixture was diluted with EtOAc (10 mL) and washed with water. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residual crude oil was purified by flash chromatography on SiO2 (0-50% EtOAc:hexanes) to afford the title compound (372 mg, 72% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.76 (dd, J=10.9, 8.3 Hz, 4H), 7.37 (d, J=7.7 Hz, 4H), 7.23 (t, J=8.0 Hz, 1H), 6.93-6.88 (m, 1H), 6.88-6.82 (m, 1H), 6.78 (dd, J=8.1, 2.3 Hz, 1H), 4.00 (s, 2H), 3.81-3.78 (m, 5H), 2.47 (s, 3H), 2.43 (s, 3H), 1.79 (s, 1H), 1.73-1.60 (m, 2H), 1.61-1.53 (m, 4H), 1.53-1.45 (m, 2H).

Provenance & Evidence