2-Cyclopenten-1-one → 5,6-Diphenyl-2,3,3a,4,7,7a-hexahydro-1H-inden-1-one

HRID 351448Notes

Reaction equation

HRID 351448 reaction equation
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH2:10])=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1(=[O:22])[CH2:21][CH2:20][CH:19]=[CH:18]1>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH2:8][CH:20]3[CH:21]([CH2:10][C:9]=2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:17](=[O:22])[CH2:18][CH2:19]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 41291332,3-Diphenyl-1,3-butadiene

Product 1

HCID 184363635,6-Diphenyl-2,3,3a,4,7,7a-hexahydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,3-diphenyl-1,3-butadiene (2.772 g, 13.44 mmol) and cyclopent-2-enone (1 eq.) was refluxed in toluene (26 mL) for 48 h. The reaction mixture was then concentrated and purified on SiO2 (20% ethyl acetate/hexane) to yield 5,6-diphenyl-2,3,3a,4,7,7a-hexahydro-inden-1-one.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified on SiO2 (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7c19c55ba5554137b65b9aace25a9630
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Reaction notes

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