Selectfluor → Ethyl 2-fluoro-3-(furan-2-yl)-3-oxopropanoate

HRID 1355860Notes

Reaction equation

HRID 1355860 reaction equation
[O:1]=[C:2]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:14][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>C(#N)C>[CH2:7]([O:6][C:4](=[O:5])[CH:3]([F:14])[C:2]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)=[O:1])[CH3:8]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 2759240Ethyl 3-(fur-2-yl)-3-oxopropanoate

Product 1

HCID 45080919Ethyl 2-fluoro-3-(furan-2-yl)-3-oxopropanoateYield 79.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the method of Banks et al. (J. Chem. Soc., Chem. Commun. 1994, 343), to a stirred solution of 10.0 g (54.9 mmol) ethyl beta-oxo-2-furanpropionate in 500 ml acetonitrile at room temperature was added 19.4 g (54.9 mmol) 1-chloromethyl-4-fluoro-1,4-diazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) and stirring continued for 90 hours at room temperature. The reaction mixture was concentrated in vacuo and the residue resuspended in ether and washed sequentially with water and with brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo to afford 8.72 g (79%) (RS)-2-fluoro-3-furan-2-yl-3-oxo-propionic acid ethyl ester as a yellow oil which was used in the next step without further purification. EI-MS m/e (%): 200 (M+, 8), 155 ([M—OEt]+, 4), 95 (100).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed sequentially with water and with brine
  3. dry with materialThe organic phase was then dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6abe0e3b5eb45af9b5ebacb7435d161
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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