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

HRID 522341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522341
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fc2e9d7deb7044aa8ad2290cc9cad7da
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09329185B2

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