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

HRID 517022노트

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HRID 517022 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f4cbe68e7f2d4c1aa31ed4716ddf1e7b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115095B2

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