Reaktion #558625

ord-bb09df4db3c347ce857da955ffe58b1a

Reaktionsgleichung

CC(C)(O)CCO
3-Methyl-1,3-butanediol
c1ccncc1
pyridine
Cc1ccc(S(=O)(=O)Cl)cc1
4-toluenesulfonyl chloride
Cc1ccc(S(=O)(=O)OCCC(C)(C)O)cc1
title compound
Cc1ccc(S(=O)(=O)OCCC(C)(C)O)cc1
Toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenthen washed with 1M aqueous hydrochloric acid
  2. 2
    Sonstigedried
  3. 3
    Sonstigethe solvent removed under vacuum
  4. 4
    SonstigeThe residue is purified by flash chromatography (0-30% ethyl acetate in cyclohexane)

Vorschrift

3-Methyl-1,3-butanediol (1.5 mL, 14.06 mmol) is suspended in dry dichloromethane (5 mL) and pyridine (1.24 mL, 15.46 mmol) is added followed by 4-toluenesulfonyl chloride (2.68 g, 14.06 mmol). The mixture is stirred overnight then washed with 1M aqueous hydrochloric acid, dried and the solvent removed under vacuum. The residue is purified by flash chromatography (0-30% ethyl acetate in cyclohexane) to give the title compound. (Yield 970 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08633182B2uspto-grants-2014_01