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

HRID 1678889Notes

Reaction equation

HRID 1678889 reaction equation
[C:1]1(=NO)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O-2].[Ca+2].[CH:11]#[CH:12].[CH3:13][N:14]([CH3:23])P(N(C)C)(N(C)C)=O>>[CH:11]([N:14]1[C:23]2[CH2:5][CH2:4][CH2:3][CH2:2][C:1]=2[CH:6]=[CH:13]1)=[CH2:12]

Participants

5

Reactant 4

HCID 6326AcetyleneHCID 7517Cyclohexanone OximeHCID 12679HexamethylphosphoramideHCID 6850728Calciumoxide

Product 1

HCID 111593881-Vinyl-4,5,6,7-tetrahydroindoleYield 30%

Procedure

5 g of cyclohexanone oxime, 0.5 g of calcium oxide in 50 ml of hexamethyltriamidophosphate are heated with a 3-fold molar excess of acetylene (with reference to the stoichiometric amount thereof) to the temperature of 170° C in a one-liter rotary autoclave (maximal pressure is 30 atm). The cooled mixture is extracted with vinyl butyl ether and the extract is distilled to give 1.8 g (yield of 30%) of 1-vinyl-4,5,6,7-tetrahydroindole.

Workup

  1. customto the temperature of 170° C
  2. extractionThe cooled mixture is extracted with vinyl butyl ether
  3. distillationthe extract is distilled

Sources & evidence

ORD record
ord-949d0fd7b9004f2b8a9f9c30895e3c86
Source dataset
uspto-grants-1978_03
Patent number
US04077975

Reaction notes

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