Ethanol → [2-(3-Methoxy-phenyl)-cyclohexyl]-acetic acid ethyl ester

HRID 418893

Reaction equation

HRID 418893 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH3:2].C(O)C>[Pd].O1CCCC1>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 193584881-(3-Methoxyphenyl)-2-(ethoxycarbonylmethyl)cyclohexene

Product 1

HCID 66651961[2-(3-Methoxy-phenyl)-cyclohexyl]-acetic acid ethyl esterYield 89.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Combine [2-(3-methoxy-phenyl)-cyclohex-1-enyl]-acetic acid ethyl ester (9.91 g, 36.0 mmol), 10% Pd on carbon (2.06 g, 14.4 mmol), and ethanol (90 mL) and tetrahydrofuran (5 mL), degas, and add 50 psi H2 at room temperature. After 18 hours, filter off the Pd catalyst over celite eluting with ethyl acetate. Concentrate and flash chromatograph with 0% to 20% ethyl acetate/hexanes to yield the titled compound (8.89 g, 89%) as a clear oil. TLC Rf=0.42 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3):1H NMR (CDCl3): 7.21 (t, 1H, J=8.1 Hz), 6.78 (d, 2H, J=7.5 Hz), 6.72 (s, 1H), 3.98 (q, 2H, J=7.0 Hz), 3.80 (m, 3H), 2.89 (m, 1H), 2.51 (m, 1H), 2.31 (m, 1H), 1.97 (m, 1H), 1.88 (m, 1H), 1.72 (m, 4H), 1.44 (m, 3H), 1.16 (t, 3H, J=6.6 Hz).

Workup

  1. additionadd 50 psi H2 at room temperature
  2. filtrationfilter off the Pd catalyst over celite
  3. washeluting with ethyl acetate
  4. concentrationConcentrate

Sources & evidence

ORD record
ord-91d9d590bfe84817ae42a4e90d6f605f
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Linked notes

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