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

HRID 1618079Notes

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 (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

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-f07d65e6e8ab40f384536807cb200664
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765966B2

Reaction notes

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