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

HRID 1877317Notes

Reaction equation

HRID 1877317 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 stiffed 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).

Workup

  1. extractionextracted tree time with EtOAc
  2. dry with materialThe combined organics layers were dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1cf39cd790e5494d83bb2c86df9f4ed5
Source dataset
uspto-grants-2012_11
Patent number
US08309737B2

Reaction notes

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