Methyl vinyl ketone → (3aRS,4SR,9aSR)-4-(3a,4,9,9a-tetrahydro-4-phenyl-benz[f]isoindolin-2-yl)-2-butanone

HRID 426758Notes

Reaction equation

HRID 426758 reaction equation
[C:1]1([CH:7]2[CH:15]3[CH:11]([CH2:12][NH:13][CH2:14]3)[CH2:10][C:9]3[CH:16]=[CH:17][CH:18]=[CH:19][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][C:21]([CH:23]=[CH2:24])=[O:22]>C(O)C>[C:1]1([CH:7]2[CH:15]3[CH:11]([CH2:12][N:13]([CH2:24][CH2:23][C:21](=[O:22])[CH3:20])[CH2:14]3)[CH2:10][C:9]3[CH:16]=[CH:17][CH:18]=[CH:19][C:8]2=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 70608213(3aRS,4SR,9aSR)-3a,4,9,9a-tetrahydro-4-phenyl-benz[f]isoindoline

Product 1

HCID 70608039(3aRS,4SR,9aSR)-4-(3a,4,9,9a-tetrahydro-4-phenyl-benz[f]isoindolin-2-yl)-2-butanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7.4 g of (3aRS,4SR,9aSR)-3a,4,9,9a-tetrahydro-4-phenyl-benz[f]isoindoline in 60 cc of ethanol is heated to the boil at reflux for 11/2 hours after the addition of 3 cc of methylvinylketone, and is subsequently concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate. After concentrating by evaporation, the filtrate yields the title compound as oily residue. Hydrogen maleate salt form: M.P. 121°-124° (after crystallization from ethanol).

Workup

  1. temperatureat reflux for 11/2 hours
  2. concentrationis subsequently concentrated by evaporation
  3. customThe residue is chromatographed on silica gel with ethyl acetate
  4. concentrationAfter concentrating by evaporation

Sources & evidence

ORD record
ord-c74ba3b8a5dc4d85bf12d8c60ec14499
Source dataset
uspto-grants-1979_10
Patent number
US04171369

Reaction notes

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