Water → 2,2,2-Trifluoro-N-(hex-5-EN-1-YL)-N-methylacetamide
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
Conditions
- Temperature
- 0 °C
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 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 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
- temperatureto warm up to room temperature
- stirringstirred for 3 days at room temperature
- extractionextracted tree time with EtOAc
- dry with materialThe combined organics layers were dried over anhydrous sodium sulphate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography on silica gel
Sources & evidence
- ORD record
- ord-217a4ce473414429aaa316a0679b8249
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09284307B2
Reaction notes
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