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

HRID 522341

反応式

HRID 522341 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fc2e9d7deb7044aa8ad2290cc9cad7da
出典データセット
uspto-grants-2016_05
特許番号
US09329185B2

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