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

Temperatur

0 °C

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

1. temperatureto warm up to room temperature
2. stirringwas stirred for 3 days
3. extractionextracted three times with EtOAc
4. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
5. customevaporated under reduced pressure
6. customThe resulting residue was purified by chromatography on silica gel (petroleum ether/EtOAc)

ORD-Eintrag

ord-9737316dae874d489c0eb63b3d304bd3

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08377962B2