Sodium ethoxide → 1-(3-Methoxyphenyl)-2-(ethoxycarbonylmethyl)cyclohexene

HRID 418892

Reaction equation

HRID 418892 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]=[C: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].[O-]CC.[Na+]>CS(C)=O>[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]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 53720108Ethyl [2-(3-methoxyphenyl)-cyclohexylidene]acetate

Product 1

HCID 193584881-(3-Methoxyphenyl)-2-(ethoxycarbonylmethyl)cyclohexeneYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Combine [2-(3-methoxy-phenyl)-cyclohexylidene]-acetic acid ethyl ester (839.4 mg, 3.06 mmol), sodium ethoxide (62.5 mg, 0.92 mmol), and DMSO (6.0 mL), stir, and heat at 100° C. After 2 hours, cool to ambient temperature and extract the organic layer with ethyl acetate. Wash the ethyl acetate layer 5× with brine and dry the organic layer over sodium sulfate, and concentrate in vacuo to yield the titled compound (769.6 mg, 92%) as a clear oil. TLC Rf=0.58 in 8:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.21 (m, 1H), 6.75 (m, 3H), 4.11 (q, 2H, J=7.2 Hz), 3.79 (s, 3H), 2.91 (s, 2H), 2.28 (m, 2H), 2.12 (m, 2H), 1.72 (m, 4H), 1.24 (t, 3H, J=7.3 Hz).

Workup

  1. temperaturecool to ambient temperature
  2. extractionextract the organic layer with ethyl acetate
  3. washWash the ethyl acetate layer 5× with brine
  4. dry with materialdry the organic layer over sodium sulfate
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-6fb12fd57b0f47369b2c163c09bed044
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Linked notes

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