Cyclohexanone → HCID 20136516, compound

HRID 579737Notes

Reaction equation

HRID 579737 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C([Li])CCC.[C:27]1(=[O:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C1(C)C=CC=CC=1.C(OCC)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[CH:12]=[C:11]([C:27]3([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[S:10][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 114037172,3-Bis(4-methoxyphenyl)thiopheneHCID 178418339Butyllithium

Product 1

HCID 20136516HCID 20136516, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,3-bis(4-methoxyphenyl)thiophene (5.92 g, 20 mmole) in toluene (20 ml)/diethyl ether (120 ml) was treated with 1.6M n-butyl lithium (14 ml, 1.1 equiv.) and heated at reflux for 1.5 hours. The reaction mixture was cooled to 0° and treated with a solution of cyclohexanone (2.3 ml, 1.1 equiv.) in 5 ml of diethyl ether. The mixture was stirred for 1.5 hours at 0° and 1 hour at room temperature, quenched with water, and extracted with ethyl acetate. The organic extracts were washed with brine, dried and concentrated in vacuo. Chromatography on a Waters Prep 500 (hexane/ethyl acetate, 3:1) provided the title compound (5.8 g, 74%) as an oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe reaction mixture was cooled to 0°
  4. customquenched with water
  5. extractionextracted with ethyl acetate
  6. washThe organic extracts were washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eecd722a154841da9ce2e8e349334df6
Source dataset
uspto-grants-1988_06
Patent number
US04749712

Reaction notes

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