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

HRID 2353531Notes

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]>C1(C)C=CC=CC=1>[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

Conditions

Temperature: 50 °C

Procedure

To a solution of tetrahydro-4H-pyran-4-one (5.0 g, 50 mmol) in 150 mL toluene at ambient temperature was added carbethoxymethylenetriphenyl phosphorane (17.4 g, 50 mmoL.). The mixture was warmed to 50° C. and allowed to stir for 16 h. The mixture was cooled to ambient temperature, concentrated under reduced pressure and purified by column chromatography (Si2O, 50% hexanes in EtOAc) to provide the title compound (2.2 g, 13 mmol, 26% yield). MS (DCI/NH3) m/z 171 (M+H)+.

Workup

temperatureThe mixture was cooled to ambient temperature
concentrationconcentrated under reduced pressure
custompurified by column chromatography (Si2O, 50% hexanes in EtOAc)

Sources & evidence

ORD record: ord-6b7c3daaa0fd49a592e2a4fe8687a4f7
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750039B2

Reaction notes

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