Beta-Nitrostyrene → Ethyl 3-nitro-2-phenylpropyl(diethoxymethyl)phosphinate

HRID 5190

반응식

HRID 5190 반응식
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:15][CH:16]([P:20]([CH3:25])(=[O:24])[O:21][CH2:22][CH3:23])[O:17][CH2:18][CH3:19])[CH3:14].[N+:26]([CH:29]=[CH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([O-:28])=[O:27].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[N+:26]([CH2:29][CH:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:25][P:20]([CH:16]([O:17][CH2:18][CH3:19])[O:15][CH2:13][CH3:14])(=[O:24])[O:21][CH2:22][CH3:23])([O-:28])=[O:27]

참가 물질

8

반응물 5

HCID 7626Beta-NitrostyreneHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 13764418Ethyl(diethoxymethyl)methylphosphinateHCID 178418339Butyllithium

생성물 1

HCID 14362826Ethyl 3-nitro-2-phenylpropyl(diethoxymethyl)phosphinate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

To a solution of 5.8 g of diisopropylamine in 40 ml of tetrahydrofuran at -78° C. under an atmosphere of nitrogen are added 35.7 ml of a 1.6M solution of n-butyllithium in hexane. This solution is then stirred for a period of 10 minutes at this temperature, after which time a solution of 10.0 g of ethyl (diethoxymethyl)methylphosphinate in 20 ml of tetrahydrofuran is added. This mixture is then stirred for a period of 1 hour at -78° C. after which time a solution of 8.5 g of β-nitrostyrene in 20 ml of tetrahydrofuran is introduced. This mixture is then allowed to warm to room temperature when 40 ml of a saturated ammonium chloride solution is added. The aqueous layer is then extracted with 2×25 ml of diethyl ether and the organic extracts are combined and dried over magnesium sulphate. The solvent is then evaporated under reduced pressure and the crude product chromatographed on silica gel using ethyl acetate as an eluent to give ethyl 3-nitro-2-phenylpropyl(diethoxymethyl)phosphinate as a viscous oil, 31 p=+42.4 and +42.0 ppm (CDCl3).

후처리

  1. additionis introduced
  2. additionis added
  3. extractionThe aqueous layer is then extracted with 2×25 ml of diethyl ether
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent is then evaporated under reduced pressure
  6. customthe crude product chromatographed on silica gel

출처 및 근거

ORD 기록
ord-5336d52842114646b59fecae49e4dd9d
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05243062

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