1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(3-Methoxyphenyl)-2-(ethoxycarbonylmethyl)cyclohexene

HRID 377308Notes

Reaction equation

HRID 377308 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=[CH:7][CH:8]=1.C1CCN2C(=NCCC2)CC1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53720108Ethyl [2-(3-methoxyphenyl)-cyclohexylidene]acetate

Product 1

HCID 193584881-(3-Methoxyphenyl)-2-(ethoxycarbonylmethyl)cyclohexeneYield 93.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of ethyl [2-(3-methoxyphenyl)-cyclohexylidene]acetate (1.5 g) in benzene (20 ml) was added 1,8-diazabicyclo[5.4.0]-7-undecene (1 ml) and the mixture was stirred for 3 days under reflux. And then the mixture was washed with water, 1N-hydrochloric acid, saturated sodium bicarbonate aqueous solution, and brine. The dried solvent was evaporated to give 1-(3-methoxyphenyl)-2-(ethoxycarbonylmethyl)cyclohexene (1.4 g).

Workup

  1. temperatureunder reflux
  2. washAnd then the mixture was washed with water, 1N-hydrochloric acid, saturated sodium bicarbonate aqueous solution, and brine
  3. customThe dried solvent was evaporated

Sources & evidence

ORD record
ord-acf6edf8314a43e0ad4b0442556d7e95
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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