Iodoethane → Tert-butyl 2-(diethoxyphosphoryl)butyrate

HRID 332584ノート

反応式

HRID 332584 の反応式
[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]

参加物

6

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetate

生成物 1

HCID 21082801Tert-butyl 2-(diethoxyphosphoryl)butyrate収率 83%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Diethylphosphonoacetic acid tert-butyl ester (1.0 g, 4.0 mmol) was dissolved in N,N-dimethylformamide (1.4 mL), 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%).

後処理

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

出典と根拠

ORDレコード
ord-b5e27736333b4106b08b1858b9669594
出典データセット
uspto-grants-2014_11
特許番号
US08877805B2

反応ノート

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