Sodium hydride → 2-(2-Fluoro-phenyl)-cyclopropanecarboxylic acid methoxy-methyl-amide

HRID 857009ノート

反応式

HRID 857009 の反応式
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=[CH:17][C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19]>CN(C=O)C>[CH3:23][O:22][N:20]([CH3:21])[C:18]([CH:17]1[CH2:4][CH:16]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[F:9])=[O:19]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 738515733-(2-fluoro-phenyl)-N-methoxy-N-methyl-acrylamide

生成物 1

HCID 587594552-(2-Fluoro-phenyl)-cyclopropanecarboxylic acid methoxy-methyl-amide収率 76.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

NaH (8 g, 60% oil dispersion) was added to a suspension of trimethylsulfoxonium iodide (44 g) in DMF (150 mL) at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for 0.5 h. A solution of 3-(2-fluoro-phenyl)-N-methoxy-N-methyl-acrylamide (19.5 g) was added to the above reaction mixture at 0° C., and the resulting reaction was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with water and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give a residue. The residue was purified by flash chromatography over silica gel (elution with 50% hexanes in ethyl acetate) to give the title compound (16 g) as an oil.

後処理

  1. customthe resulting reaction
  2. temperatureto warm to room temperature
  3. stirringstirred for 2 h
  4. customThe reaction was quenched with water
  5. extractionthe aqueous layer was extracted with CH2Cl2
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto give a residue
  10. customThe residue was purified by flash chromatography over silica gel (elution with 50% hexanes in ethyl acetate)

出典と根拠

ORDレコード
ord-ba2d9ff610634dbea4c5253658474c71
出典データセット
uspto-grants-2006_12
特許番号
US07144881B2

反応ノート

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