4-Toluenesulfonyl chloride → toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester

HRID 470314

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:11])[CH2:9][O:10][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a mixture of (S)-1-(3-Chloro-phenyl)-ethane-1,2-diol (9.83 g, 0.057 mol) and triethylamine (11.8 ml, 0.086 mol) a solution of TsCl (10.87 g, 0.057 mol) in dichloromethane (50 ml) was added at 0° C. over 30 min. The mixture was stirred at 0° C. for 4 h. Precipitate formed was removed by filtration, the filtrate was washed with water (50 ml), dried over Na2SO4, evaporated. The residue vas dissolved in CH2Cl2 (200 ml), filtered through a SiO2 pad, evaporated. Colorless oil, 16.34 g (0.050 mol, 88%). 1H NMR (300 MHz, DMSO) δ 7.67 (d, J=8.5 Hz, 2H), 7.42 (d, J=8.5 Hz, 2H), 7.20-7.35 (m, 4H), 5.90 (d, J=4.9 Hz, 1H), 4.79 (q, J=5.1 Hz, 1H), 4.03 (m, 2H), 2.41 (s, 3H)

Aufarbeitung

additionwas added at 0° C. over 30 min
customPrecipitate formed
customwas removed by filtration
washthe filtrate was washed with water (50 ml)
dry with materialdried over Na2SO4
customevaporated
dissolutionThe residue vas dissolved in CH2Cl2 (200 ml)
filtrationfiltered through a SiO2 pad
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-6712fe730cb54016a36539127c6af5fa
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08629147B2

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