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

HRID 1678893Notes

Reaction equation

HRID 1678893 reaction equation
[C:1]1(=[N:7]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].CS(C)=O.[CH:15]#[CH:16].[CH2:17](OCC)[CH3:18]>O1CCOCC1>[CH:15]([N:7]1[C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=2[CH:18]=[CH:17]1)=[CH2:16]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 6326AcetyleneHCID 7517Cyclohexanone OximeHCID 14797Potassium Hydroxide

Product 1

HCID 111593881-Vinyl-4,5,6,7-tetrahydroindoleYield 91.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5 g of cyclohexanone oxime, 1 g of potassium hydroxide, 50 ml of dimethylsulfoxide and 50 ml of dioxane are heated for a period of one hour at the temperature of 140° C in the presence of a 5-fold excess of acetylene (with respect to the stoichiometric amount thereof). After extraction with diethyl ether and distillation 5.4 g (yield is 91.6%) of 1-vinyl-4,5,6,7-tetrahydroindole are obtained.

Workup

  1. extractionAfter extraction

Sources & evidence

ORD record
ord-9cff0faa917246d8b95adbf38e874681
Source dataset
uspto-grants-1978_03
Patent number
US04077975

Reaction notes

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