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

HRID 561900

Reaktionsgleichung

Reaktionsgleichung von HRID 561900
[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

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10130180(S)-1-(3-Chlorophenyl)ethane-1,2-diol

Produkt 1

HCID 15442725toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

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 and evaporated. The residue was dissolved in CH2Cl2 (200 mL), filtered through a SiO2 pad and evaporated. Colorless oil, 16.34 g (0.050 mol, 88%).

Aufarbeitung

  1. additionwas added at 0° C. over 30 min
  2. customPrecipitate formed
  3. customwas removed by filtration
  4. washthe filtrate was washed with water (50 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. dissolutionThe residue was dissolved in CH2Cl2 (200 mL)
  8. filtrationfiltered through a SiO2 pad
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8d03068d724c450685475f7858443071
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063225B2

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