Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 3-Methyl-hept-2-enedioic acid dimethyl ester, E

HRID 626864Notes

Reaction equation

HRID 626864 reaction equation
O=[CH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[C:10]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH2:13]C)=[O:11]>C1(C)C=CC=CC=1>[C:10]([O:12][CH3:13])(=[O:11])/[CH:15]=[CH:2]/[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 554053Pentanoic acid, 5-oxo-, methyl ester

Product 1

HCID 64295883-Methyl-hept-2-enedioic acid dimethyl ester, EYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 5-oxopentanoate (1.9 g, 14.6 mmol) and (carboethoxymethylene) triphenylphosphorane (5.0 g, 14.9 mmol) in toluene (50 mL) was refluxed for 8 hours. Solvent was removed under vacuo and the crude was purified by flash chromatography on silica gel (eluant: AcOEt/hexane 2/8) to give 1.32 g (48% yield) as colorless oil of the title compound.

Workup

  1. customSolvent was removed under vacuo
  2. customthe crude was purified by flash chromatography on silica gel (eluant: AcOEt/hexane 2/8)

Sources & evidence

ORD record
ord-8c98136f68ea4e76ae873c363dfc477e
Source dataset
uspto-grants-2016_04
Patent number
US09309253B2

Reaction notes

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