Iodoethane → Tert-butyl 2-(diethoxyphosphoryl)butyrate

HRID 517315노트

반응식

HRID 517315 반응식
[C:1]([O:5][C:6](=[O:16])[CH2:7][P:8]([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:19](I)[CH3:20]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:16])[CH:7]([P:8]([O:10][CH2:11][CH3:12])([O:13][CH2:14][CH3:15])=[O:9])[CH2:19][CH3:20])([CH3:3])([CH3:2])[CH3:4]

참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetate

생성물 1

HCID 21082801Tert-butyl 2-(diethoxyphosphoryl)butyrate수율 83%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Diethylphosphonoacetic acid tert-butyl ester (1.0 g, 4.0 mmol) was dissolved in N,N-dimethylformamide (1.4 and 60% sodium hydride (0.17 g, 4.4 mmol) was added at 0° C. After stirring at room temperature for 30 minutes, the reaction mixture was cooled again to 0° C., ethyl iodide (0.33 mL, 4.1 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed successively with 0.5N hydrochloric acid, water and saturated brine, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=57/43) to give the title compound (0.92 g, 3.3 mmol, 83%).

후처리

  1. additionwas added at 0° C
  2. temperaturethe reaction mixture was cooled again to 0° C.
  3. stirringthe mixture was stirred at room temperature overnight
  4. washwashed successively with 0.5N hydrochloric acid, water and saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=57/43)

출처 및 근거

ORD 기록
ord-420e509b318a4bfabf2548095802a895
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115107B2

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