Iodoethane → Tert-butyl 2-(diethoxyphosphoryl)butyrate

HRID 1913569ノート

反応式

HRID 1913569 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-b2902073f9b2404294b6db9c4b2c8911
出典データセット
uspto-grants-2013_12
特許番号
US08609715B2

反応ノート

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