Acetic Anhydride → N-[2-(3-fluoro-2-hydroxyphenyl)ethyl]acetamide

HRID 1176377ノート

反応式

HRID 1176377 の反応式
[F:1][C:2]1[C:3]([OH:11])=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[F:1][C:2]1[C:3]([OH:11])=[C:4]([CH2:8][CH2:9][NH:10][C:12](=[O:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 4311764Sodium borohydrideHCID 684994132-(3-Fluoro-2-hydroxyphenyl)acetonitrile

生成物 1

HCID 68502069N-[2-(3-fluoro-2-hydroxyphenyl)ethyl]acetamide

試薬・触媒・溶媒 2

HCID 11791229Dichloronickel;hexahydrate触媒HCID 887Methanol溶媒

実験手順

A solution of 1.54 g of (3-fluoro-2-hydroxyphenyl)acetonitrile, 1.87 ml of acetic anhydride and 2.41 g of nickel chloride hexahydrate in 75 ml of methanol is admixed at 0° C. with 2.72 g of sodium borohydride in portions and stirred at room temperature over 22 hours. The reaction mixture is concentrated by evaporation, and the residue is diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution and clarified by filtration. The aqueous phase is extracted with ethyl acetate (3×). The combined organic phases are dried with sodium sulphate and concentrated by evaporation. The title compound is obtained as a beige solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.23 (95:5 dichloromethane-methanol); Rt=2.60.

後処理

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. additionthe residue is diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. filtrationclarified by filtration
  4. extractionThe aqueous phase is extracted with ethyl acetate (3×)
  5. dry with materialThe combined organic phases are dried with sodium sulphate
  6. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-cb1072cb16dd469882f979af86bc25f6
出典データセット
uspto-grants-2010_11
特許番号
US07842688B2

反応ノート

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