Toluene → Ethyl 6-cyano-4,4-diphenyl-hex-2-enoate

HRID 1602161Notes

Reaction equation

HRID 1602161 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(C=O)[CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([CH:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:22][CH2:23][CH3:24])=[O:21].[C:45]1(C)C=CC=CC=1>>[C:10]([CH2:9][CH2:8][C:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:45]=[CH:25][C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:11]

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 196102744,4-Diphenyl-4-formylbutanenitrile

Product 1

HCID 54399157Ethyl 6-cyano-4,4-diphenyl-hex-2-enoate

Procedure

A mixture of 4,4-diphenyl-4-formylbutyronitrile (8.04 g) and (carbethoxymethylene)-triphenylphosphorane (20.85 g) in toluene (200 mL) was heated under reflux for 3 days. The reaction mixture was concentrated in vacuo and the residue was purified by a silica gel column chromatography to give the desired product as a yellow-orange oil (12.10 g): MS showed (M+NH4)+ @ 337; 1H-NMR (CDCl3, δ): 1.25-1.32 (t. 3H), 2.10-2.18 (m, 2H), 2.65-2.75 (m, 2H), 4.15-4.23 (q, 2H), 5.60-5.66 (d. 1H), 7.05-7.75 (m. I 1H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-598ba20dc39d45c1bd682e6cb5eefed8
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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