Acetylene → 1-Vinyl-4,5,6,7-tetrahydroindole

HRID 1678891Notes

Reaction equation

HRID 1678891 reaction equation
[C:1]1(=[N:7]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9](O)(CC)(C)[CH3:10].[CH:15]#[CH:16]>CS(C)=O>[CH:15]([N:7]1[C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=2[CH:10]=[CH:9]1)=[CH2:16]

Participants

5

Reactant 3

HCID 6326AcetyleneHCID 64052-Methyl-2-butanolHCID 7517Cyclohexanone Oxime

Product 1

HCID 111593881-Vinyl-4,5,6,7-tetrahydroindoleYield 94.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5 g of cyclohexanone oxime, 1 g of potassium tert.amylate, 125 ml of dimethylsulfoxide and 125 ml of tert-amyl alcohol are heated for a period of 3 hours at a temperature of 120° C in a one-liter rotary autoclave in the presence of a 4-fold excess of acetylene (with respect to the stoichiometric amount thereof). Maximal pressure is 29 atm. The reaction mixture is extracted with diethyl ether and distilled to give 5.6 g (94.9%) of 1-vinyl-4,5,6,7-tetrahydroindole.

Workup

  1. extractionThe reaction mixture is extracted with diethyl ether
  2. distillationdistilled

Sources & evidence

ORD record
ord-218edfcad65d42e28427ddfc97895c94
Source dataset
uspto-grants-1978_03
Patent number
US04077975

Reaction notes

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