반응 #800727

반응 방정식

5,5,5-trifluoro-2-phenylpentan-2-ol

triethylamine

methacryloyl chloride

→

5,5,5-trifluoro-2-phenylpentan-2-yl methacrylate

수율 72.0%

용매

methylene chloride

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas slowly charged into flask
2. 2
   기타equipped with magnetic stirrer
3. 3
   기타Upon completion of the reaction
4. 4
   기타the mixture was quenched
5. 5
   workup.ADDITIONby pouring into 400 mL of deionized water
6. 6
   추출extracted further into methylene chloride
7. 7
   건조The methylene chloride extracts were then dried over sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo

실험 절차

21 g of 5,5,5-trifluoro-2-phenylpentan-2-ol (5) and 11.6 g of triethylamine dissolved in 40 mL of methylene chloride was slowly charged into flask equipped with magnetic stirrer and 11 ml, of methacryloyl chloride in 100 mL of dichloromethane cooled down to 0° C. The resultant mixture slowly warmed up to room temperature and allowed to stir at this temperature for 12 hours. Upon completion of the reaction as confirmed by thin layer chromatography, the mixture was quenched by pouring into 400 mL of deionized water and extracted further into methylene chloride. The methylene chloride extracts were then dried over sodium sulfate, filtered and concentrated in vacuo affording 20 g of 5,5,5-trifluoro-2-phenylpentan-2-yl methacrylate (LG2) (˜72% yield) of as an amber oil. The oil was purified further by passing through a silica gel plug and eluting with a 70:30 mixture of hexanes/methylene chloride to afford 19 g of pure product. 1H NMR (500 MHz, Acetone-d6): δ 7.32 (s, 3H), 7.24 (s, 2H), 6.11 (s, 1H, vinyl), 5.6 (s, 1H, vinyl), 2.45-2.05 (m/m, 5H), 1.92 (s, 3H), 1.87 (s, 3H).

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