Hexane → 1,1,1-Trifluoro-4-phenyl-but-3-yn-2-one

Temperature

0 °C

Phenylacetylene (10.8 mL, 0.098 mole) was added into a 3-Neck round bottom flask under an atmosphere of Nitrogen. THF (100 mL) was added and the reaction was stirred and cooled to 0° C. 2.5 M n-butyllithium in hexane (36 mL, 0.089 mole) was added via syringe at 0° C. over 30 min. The reaction was stirred at 0° C. for 30 minutes. Ethyl trifluoroacetate (5.31 mL, 0.045 mole) was added via syringe at −60 to −50° C. over 10 minutes. The reaction was stirred at −70° C. for 1 h. Ammonium chloride 28% w/w in water (60 mL) was added and the mixture was extracted with Ether (2×50 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo, and then allowed to stand under high vacuum for 2 h to afford an orange oil. The oil was chromatographed on silica gel with 2:1 hexanes, methylene chloride to afford the title compound as a yellow oil; 1H NMR (CDCl3, 400 MHz) δ 7.44-7.48 (tt, 2H), 7.55-7.60 (tt, 1H), 7.67-7.70 (m, 2 H); 19F NMR (CDCl3, 400 MHz) δ 77.54 (s).

1. stirringThe reaction was stirred at 0° C. for 30 minutes
2. stirringThe reaction was stirred at −70° C. for 1 h
3. extractionthe mixture was extracted with Ether (2×50 mL)
4. dry with materialThe organic phase was dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto afford an orange oil
8. customThe oil was chromatographed on silica gel with 2:1 hexanes, methylene chloride

ORD record

ord-ba223d4f925e4d16a14d4ddce9c0d844

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735405B2