Dimethyl Sulfoxide → 1-Vinyl-4,5,6,7-tetrahydroindole

HRID 1678892Notes

Reaction equation

HRID 1678892 reaction equation
[C:1]1(=[N:7]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].CS(C)=O.[CH:15]#[CH:16].N1C=CC=[CH:19][CH:18]=1>>[CH:15]([N:7]1[C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=2[CH:19]=[CH:18]1)=[CH2:16]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 6326AcetyleneHCID 7517Cyclohexanone OximeHCID 14798Sodium Hydroxide

Product 1

HCID 111593881-Vinyl-4,5,6,7-tetrahydroindoleYield 90%

Procedure

5 g of cyclohexanone oxime, 2.5 g of sodium hydroxide, 100 ml of dimethylsulfoxide and 5 ml of pyridine are heated for 3 hours at a temperature of 90° C in a one-liter rotary autoclave in the presence of a 5-fold excess of acetylene (with respect to the stoichiometric amount thereof). Maximal pressure is 27 atm. The reaction mixture is extracted with diethyl ether and distilled to give 5.3 g (90%) 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-79786a842a774cd38cf461162f1951d3
Source dataset
uspto-grants-1978_03
Patent number
US04077975

Reaction notes

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