Cyclohexane → 1-allyl-1H-pyrrole-2-carbonitrile

HRID 542860Notes

Reaction equation

HRID 542860 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]=O)[CH:2]=[CH2:3].C([N:14]1C=CC=C1C=O)(C)C.C1CCCCC1>ClCCl>[CH2:1]([N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]#[N:14])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 31559701-Isopropyl-1H-pyrrole-2-carbaldehydeHCID 109424801-Allyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 135893111-allyl-1H-pyrrole-2-carbonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the same manner as described in Reference Example 2 (1) except that 1-allylpyrrole-2-carbaldehyde (prepared in the same manner as described in Can. J. Chem., 55, 4112, 1977, b.p. 80°-83° C./7 mmHg) (8.1 g, 60 mmole) is used instead of 1-isopropylpyrrole-2-carbaldehyde and further the product is isolated by silica gel column chromatography (solvent, cyclohexane:dichloromethane=3:1) instead of distillation under reduced pressure, there is obtained 1-allylpyrrole-2-carbonitrile (4.0 g, yield: 50%).

Workup

  1. customprepared in the same manner

Sources & evidence

ORD record
ord-b4583f28c3ea49f6abb5e5a3e38595c8
Source dataset
uspto-grants-1987_04
Patent number
US04659726

Reaction notes

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