Toluene → ethyl cyano-[4-(1E-pentenyl)cyclohexylidene]acetate

HRID 1109694Notes

Reaction equation

HRID 1109694 reaction equation
[CH:1](/[CH:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5].[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14].C1(C)C=CC=CC=1.C([O-])(=O)C.[NH2+]1CCCCC1>O>[C:13]([C:15](=[C:9]1[CH2:10][CH2:11][CH:6](/[CH:1]=[CH:2]/[CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7764Ethyl cyanoacetateHCID 3014295Piperidinium acetateHCID 190192404-(1E-pentenyl)cyclohexanone

Product 1

HCID 19019238ethyl cyano-[4-(1E-pentenyl)cyclohexylidene]acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 33.3 g of 4-(1E-pentenyl)cyclohexanone (prepared in accordance with EP-A-168683), 42 ml of ethyl cyanoacetate, 300 ml of toluene and 2.9 g of piperidinium acetate is boiled for 1.5 hours on a water separator. After cooling the reaction mixture is washed with three 50 ml portions of water, dried over sodium sulphate and concentrated. Chromatographic purification of the residue on 750 g of silica gel with hexane/ethyl acetate (vol. 19:1) gives ethyl cyano-[4-(1E-pentenyl)cyclohexylidene]-acetate.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washis washed with three 50 ml portions of water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customChromatographic purification of the residue on 750 g of silica gel with hexane/ethyl acetate (vol. 19:1)

Sources & evidence

ORD record
ord-586d105dc3704e77b6d2b9173fd40d2e
Source dataset
uspto-grants-1994_06
Patent number
US05322638

Reaction notes

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