Tetrahydrofuran → Diethyl 2-fluoro-2-phenylmalonate

HRID 2259399

反応式

HRID 2259399 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 4246642Diethyl 2-fluoro-2-phenylmalonate収率 65%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bff8bed15d45475c8f836dbd9ebfd39d
出典データセット
uspto-grants-1995_12
特許番号
US05473065

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