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

HRID 1176377노트

반응식

HRID 1176377 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 11791229Dichloronickel;hexahydrate촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb1072cb16dd469882f979af86bc25f6
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

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