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

HRID 1515753Notes

Reaction equation

HRID 1515753 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(#N)C>[CH2:11]([O:10][C:8](=[O:9])[CH:13]=[C:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[CH3:12]

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 63.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tetrahydro-pyran-4-one (25 g, 0.25 mol) in acetonitrile (250 mL) was added (carbethoxymethylene)triphenylphosphorane (96 g, 0.28 mol) at room temperature. The resulting mixture was heated at 70° C. for 16 h. The reaction mixture concentrated in vacuo. Purification by flash column chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 30% ethyl acetate/hexanes) afforded (tetrahydro-pyran-4-ylidene)-acetic acid ethyl ester (27 g, 63%) as a yellow oil.

Workup

  1. concentrationThe reaction mixture concentrated in vacuo
  2. customPurification by flash column chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9c4b30b4db134fa6aaca14c1c24c2545
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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