Diiodomethane → N-[4-Chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl]acetamide

HRID 588869ノート

反応式

HRID 588869 の反応式
[Cl:1][C:2]1[C:7]([C:8]([CH3:10])=[CH2:9])=[CH:6][C:5]([NH:11][C:12](=[O:14])[CH3:13])=[C:4]([O:15][CH3:16])[CH:3]=1.[CH2:17](I)I.[Zn](CC)CC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]2([CH3:17])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:11][C:12](=[O:14])[CH3:13])=[C:4]([O:15][CH3:16])[CH:3]=1

参加物

5

反応物 3

HCID 6346DiiodomethaneHCID 90455956N-[4-Chloro-2-methoxy-5-(1-methylethenyl)phenyl]acetamideHCID 178418750HCID 178418750、化合物

生成物 1

HCID 90455914N-[4-Chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl]acetamide収率 77.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of N-(4-chloro-2-methoxy-5-(prop-1-en-2-yl)phenyl)acetamide (1.0 g, 4.17 mmol) in toluene (20 mL) at 0° C., CH2I2 (5.6 g, 20.86 mmol) and Et2Zn (41.7 mL, 41.7 mmol, 1.0 M in hexane) was added. The mixture was kept at 0° C. for 30 min, and then stirred at RT for 16 h. The reaction mixture was quenched with saturated NH4Cl solution and stirred for 15 min. The mixture was concentrated in vacuo to remove toluene and the resulting mixture was extracted with dichloromethane. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4, concentrated to afford the desired product (820 mg, 77% yield).

後処理

  1. customThe reaction mixture was quenched with saturated NH4Cl solution
  2. stirringstirred for 15 min
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove toluene
  5. extractionthe resulting mixture was extracted with dichloromethane
  6. washThe combined organic layer was washed with water and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-57134825d82a4f77a7bc2fc95323b3a2
出典データセット
uspto-grants-2016_01
特許番号
US09227978B2

反応ノート

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