Sodium hydride → Ethyl 3-trifluoromethanesulfonyloxy-2-heptenoate

HRID 1646124

Reaction equation

HRID 1646124 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].C1(N[S:22]([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23])C=CC=CC=1.CCOCC.CCCCCC>CN(C)C=O.CCOCC.O>[F:26][C:25]([F:28])([F:27])[S:22]([O:1][C:2]([CH2:9][CH2:10][CH2:11][CH3:12])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:24])=[O:23]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 559036Ethyl 3-oxoheptanoateHCID 21584099Diethylether hexane

Product 1

HCID 54561069Ethyl 3-trifluoromethanesulfonyloxy-2-heptenoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584184Diethylether waterSolvent

Procedure

Ethyl 3-ketoheptanoate (2.07 g, 12 mmol) was dissolved in dimethylformamide (60 mL) under argon and sodium hydride (357 mg, 14.4 mmol) was added. After 30 minutes at room temperature the solid N-phenyltrifluoromethanesulfonamide (Tetra. Letters, (1983), 24, 979) (4.97 g, 13.8 mmol) was added. The reaction was stirred for 2 hours, diluted with ether/water and the usual workup gave after chromatography with 5:95 ether/hexane 3.45 g (94%) of ethyl 3-trifluoromethanesulfonyloxy-2-heptenoate.

Sources & evidence

ORD record
ord-fedca15b93d04a8a8a666e1fa2bd064e
Source dataset
uspto-grants-1993_01
Patent number
US05177096

Linked notes

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