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

HRID 1294567ノート

反応式

HRID 1294567 の反応式
[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

参加物

5

反応物 2

HCID 23106215N-(3-fluoro-2-formyl-phenyl)-acetamideHCID 178424303HCID 178424303、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-db1a1fd68485452d9be4959907fbf2e0
出典データセット
uspto-grants-2007_07
特許番号
US07241769B2

反応ノート

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