Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 76563139, compound

HRID 548628Notes

Reaction equation

HRID 548628 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:33][C:34]([O:36][CH3:37])=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=[CH:33][C:34]([O:36][CH3:37])=[O:35])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 698901-Benzyl-3-pyrrolidinone

Product 1

HCID 76563139HCID 76563139, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-benzylpyrrolidin-3-one a43 (8.75 g, 50 mmol, 1 eq) is dissolved in toluene (100 ml). Methyl (triphenylphosphoranylidene)acetate a44 (18.4 g, 55 mmol, 1.1 eq) is added and the mixture is refluxed for 60 h. The cold suspension is then filtered and the filtrate is concentrated to dryness. The crude product is purified by chromatography over silicagel (ethyl acetate/hexane 10/90) to afford 7.2 g of pure methyl (1-benzylpyrrolidin-3-ylidene)acetate a45.

Workup

  1. temperaturethe mixture is refluxed for 60 h
  2. filtrationThe cold suspension is then filtered
  3. concentrationthe filtrate is concentrated to dryness
  4. customThe crude product is purified by chromatography over silicagel (ethyl acetate/hexane 10/90)

Sources & evidence

ORD record
ord-9f034e1335e94b19b869bb49da883014
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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