Toluene → HCID 53674676, compound

HRID 1602174Notes

Reaction equation

HRID 1602174 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH2:12]C=O)[CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([CH:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23][CH3:24])=[O:22].[C:45]1(C)C=CC=CC=1>>[C:10]([CH2:9][CH2:8][C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:12][CH:45]=[CH:25][C:21]([O:23][CH3:24])=[O:22])#[N:11]

Participants

4

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 19610222HCID 19610222, compound

Product 1

HCID 53674676HCID 53674676, compoundYield 69%

Procedure

A mixture of 4,4-diphenyl-5-formylpentanonitrile (1.87 g, 7.1 mmol) and (carbomethoxymethylene)triphenyl phosphorane (2.85 g. 8.5 mmol) in toluene (50 mL) was heated under reflux for three days. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography to give the desired product as a colorless oil (1.56 g 69%): MS showed (M+H)+ c 320: 1H-NMR (CDCl3, δ): 1.97-2.0(m. 2H), 2.44-2.51 (m. 2H), 3.00 (dd, 2H, J=1.4, 7.4 Hz), 3.68 (s, 3H), 5.82 (dt, 1H, J=l.4. 15.6 Hz), 6.52 (dt, 1H. J=7.3, 15.6 Hz), 7.10-7.55 (m, 4H), 7.21-7.35 (m, 6H); Anal. Calcd for C,,H21NO2 : C. 78.97; H. 6.63; N, 4.39; Found: C, 78.68; H, 6.85; N. 4.27.

Workup

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

Sources & evidence

ORD record
ord-5a0cbd0231d643a899fedc2782b0b653
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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