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

HRID 1855031Notes

Reaction equation

HRID 1855031 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C:13]2([CH2:20][O:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([Mg]Br)[CH:37]=[CH:38][CH:39]=1>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][C:13]2([CH2:20][O:21][S:22]([C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)(=[O:24])=[O:23])[CH2:18][CH2:17][C:16]([OH:19])([C:38]3[CH:37]=[CH:36][CH:35]=[C:34]([O:33][CH3:32])[CH:39]=3)[CH2:15][CH2:14]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 88538615(4-Oxocyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)HCID 178490745HCID 178490745, compound

Product 1

HCID 90408498(4-Hydroxy-4-(3-methoxyphenyl)cyclohexane-1,1-diyl)bis(methylene) bis(4-methylbenzenesulfonate)Yield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e9a760a05c3747739f2e7a9cdc815ed0
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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