S-Methyl methanethiosulfonate → Trifluoro-1-(4-methyldisulfanyl-phenyl)-ethanol

HRID 522341

반응식

HRID 522341 반응식
[CH3:1][S:2][S:3]([CH3:6])(=O)=O.[F:7][C:8]([F:19])([F:18])[CH:9]([C:11]1[CH:16]=[CH:15]C(S)=[CH:13][CH:12]=1)[OH:10]>CCO.C1COCC1>[F:7][C:8]([F:18])([F:19])[CH:9]([C:11]1[CH:16]=[CH:15][C:1]([S:2][S:3][CH3:6])=[CH:13][CH:12]=1)[OH:10]

참가 물질

5

반응물 2

HCID 18064S-Methyl methanethiosulfonateHCID 904025372,2,2-Trifluoro-1-(4-mercapto-phenyl)-ethanol

생성물 1

HCID 90402522Trifluoro-1-(4-methyldisulfanyl-phenyl)-ethanol수율 86%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

Methanethiosulfonic acid S-methyl ester (0.02 ml, 0.22 mmol) was dissolved in an EtOH (0.46 mL) and saturated NaCO3/H2O (pH 8) solution (0.8 mL) under argon at 0° C. A solution of 2,2,2-trifluoro-1-(4-mercapto-phenyl)-ethanol (5) (22 mg, 0.11 mmol) dissolved in THF (1.5 mL) under argon was added dropwise. After 10 minutes, the reaction temperature was raised to room temperature. After 36 hours, the reaction was extracted with ethyl acetate (3×30 mL) and H2O (30 mL). The combined organic phases were dried over Na2SO4 and under reduced pressure. Flash chromatography on silica gel using 0-30% acetone/hexane gave Compound 15 as a yellow oil (23 mg, 86% yield). 1H NMR (400 MHz, CDCl3): δ 7.5 (m, 4H), 5.02 (q, J=6.7 Hz, 1H), 2.45 (s, 3H); 19F NMR (376 Hz, CDCl3) δ −78.79 (d); 13C NMR (100 MHz, CH3OD): δ 137.6, 134.2, 128.8, 126.4, 124.6 (q, JCF=281.7 Hz), 71 (q, JCF=31.5 Hz), 21.5.

후처리

  1. additionwas added dropwise
  2. waitAfter 36 hours
  3. extractionthe reaction was extracted with ethyl acetate (3×30 mL) and H2O (30 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4 and under reduced pressure

출처 및 근거

ORD 기록
ord-fc2e9d7deb7044aa8ad2290cc9cad7da
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09329185B2

연결된 노트

불러오는 중…