Water → 2,2,2-Trifluoro-N-(hex-5-EN-1-YL)-N-methylacetamide

HRID 448846ノート

反応式

HRID 448846 の反応式
[H-].[Na+].[CH3:3][NH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17].O>CN(C=O)C>[F:7][C:6]([F:9])([F:8])[C:5]([N:4]([CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[CH2:12])[CH3:3])=[O:10]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69948Acetamide, 2,2,2-trifluoro-N-methyl-HCID 759066-Bromo-1-hexene

生成物 1

HCID 575787592,2,2-Trifluoro-N-(hex-5-EN-1-YL)-N-methylacetamide収率 56%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (60% dispersion in mineral oil, 31.5 g, 1.28 eq.) was slowly added under nitrogen atmosphere to a solution of N-methyl-2,2,2-trifluoroacetamide (100 g, 1.28 eq.) in DMF (500 mL) at 0° C. The reaction mixture was stirred for 90 min at 0° C., and then 6-bromo-1-hexene (100 g, 1 eq.) was added dropwise over 45 min. The reaction mixture was allowed to warm up to room temperature, and stirred for 3 days at room temperature. The reaction mixture was then poured into water and extracted tree time with EtOAc. The combined organics layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to produce compound 31a as colorless oil in 56% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 1.27-1.38 (m, 2H), 1.48-1.60 (m, 2H), 2.00-2.06 (m, 2H), 2.93-3.07 (2m, 3H), 3.35-3.40 (m, 2H), 4.92-5.04 (m, 2H), 5.73-5.83 (m, 1H).

後処理

  1. temperatureto warm up to room temperature
  2. stirringstirred for 3 days at room temperature
  3. extractionextracted tree time with EtOAc
  4. dry with materialThe combined organics layers were dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-bb21e36866ab46998faf6150d3b7b65f
出典データセット
uspto-grants-2013_07
特許番号
US08481748B2

反応ノート

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