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

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).

1. customquenched with sat′d aqueous NH4Cl (1 mL)
2. additionThe mixture was diluted with EtOAc (10 mL)
3. washwashed with water
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residual crude oil was purified by flash chromatography on SiO2 (0-50% EtOAc:hexanes)

ORD record

ord-e9a760a05c3747739f2e7a9cdc815ed0

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962660B2