Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 2-(oxan-4-ylidene)acetate

HRID 1597427Notes

Reaction equation

HRID 1597427 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[C:8]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:10][CH2:11][CH3:12])=[O:9]>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][C:4](=[CH:13][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 11105795Ethyl 2-(oxan-4-ylidene)acetateYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tetrahydo-4H-pyran-4-one (5 g, 50 mmol) in CH2Cl2 (500 mL) was treated with (carbethoxymethylene)triphenylphosphorane (19.29 g, 55 mmol) stirred at reflux for 24 h, concentrated and purified via silica gel column chromatography eluting with 10% ethyl acetate/hexane to give 4.8 g of the title compound. MS (APCI): m/z 188 (M+NH4)+.

Workup

  1. temperatureat reflux for 24 h
  2. concentrationconcentrated
  3. custompurified via silica gel column chromatography
  4. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7c4dfa452ebc4545b54c9fae20d8e30b
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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