Tetrahydrofuran → Diethyl 2-fluoro-2-phenylmalonate

HRID 2259399

반응식

HRID 2259399 반응식
[Na][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].O1CCCC1.[O-]S(C(F)(F)[F:29])(=O)=O.[O-]S(C(F)(F)F)(=O)=O.F[N+]12CC[N+](F)(CC1)CC2>C(#N)C.C(OCC)C>[F:29][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 152179651,4-Difluoro-1,4-diazoniabicyclo[2.2.2]octane bistriflateHCID 178472663C13H15NaO4

생성물 1

HCID 4246642Diethyl 2-fluoro-2-phenylmalonate수율 65%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

A cold (-10° C.) solution of diethyl sodio(phenyl)-malonate in anhydrous tetrahydrofuran [prepared in conventional fashion from sodium hydride (2.5 mmol) and diethyl phenylmalonate (0.5 g, 2.1 mmol) in THF (15 cm3)] was added slowly to a cold (-10° C.) stirred solution of 1,4-difluoro-1,4-diazoniabicyclo[2.2.2]octane bistriflate (0.95 g, 2.12 mmol) in dry acetonitrile (50 cm3) under an atmosphere of nitrogen. The reaction mixture was allowed to warm to room temperature and then diluted with diethyl ether (100 cm3). The mixture was then washed with 0.5M oxalic acid (30 cm3), 10% aqueous potassium hydrogen carbonate (30 cm3), and saturated brine (30 cm3) (in that order), dried (MgSO4), filtered, and the filtrate evaporated under reduced pressure to provide diethyl fluoro(phenyl)-malonate (65% yield) with correct NMR parameters.

후처리

  1. washThe mixture was then washed with 0.5M oxalic acid (30 cm3), 10% aqueous potassium hydrogen carbonate (30 cm3), and saturated brine (30 cm3) (in that order)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe filtrate evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-bff8bed15d45475c8f836dbd9ebfd39d
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05473065

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