N-(3-fluoro-2-formyl-phenyl)-acetamide → N-[3-fluoro-2-(hydroxyl-o-tolyl-methyl)-phenyl]-acetamide

HRID 1294567노트

반응식

HRID 1294567 반응식
[F:1][C:2]1[C:3]([CH:12]=[O:13])=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[C:14]1([CH3:22])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Mg]Br>O1CCCC1.C(OCC)C>[F:1][C:2]1[C:3]([CH:12]([OH:13])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH3:22])=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 23106215N-(3-fluoro-2-formyl-phenyl)-acetamideHCID 178424303HCID 178424303, 화합물

생성물 1

HCID 69489997N-[3-fluoro-2-(hydroxyl-o-tolyl-methyl)-phenyl]-acetamide

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

100 mg (0.83 mmol) N-(3-fluoro-2-formyl-phenyl)-acetamide are dissolved in 4 ml of tetrahydrofuran and cooled to −78° C. Then at this temperature 1.66 ml (3.3 mmol) of a 2 M solution of o-tolylmagnesium bromide in diethyl ether are added. This reaction mixture is thawed to ambient temperature overnight with stirring. Then the reaction mixture is stirred into 30 ml dist. water and extracted three times with 10 ml of ethyl acetate. The organic phase is dried with MgSO4, the solvent is eliminated in vacuo. The crude product is purified by column chromatography. The carrier material used is silica gel and the eluant used is a mixture of cyclohexane:ethyl acetate (80:20).

후처리

  1. stirringThen the reaction mixture is stirred into 30 ml dist
  2. extractionwater and extracted three times with 10 ml of ethyl acetate
  3. dry with materialThe organic phase is dried with MgSO4
  4. customThe crude product is purified by column chromatography
  5. additiona mixture of cyclohexane:ethyl acetate (80:20)

출처 및 근거

ORD 기록
ord-db1a1fd68485452d9be4959907fbf2e0
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241769B2

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