Reaktion #93921

ord-542ca5e3dfdf496daa193719263b12ae

Reaktionsgleichung

O=C=O
carbon dioxide
CCCCCC(CCCC(CC#CCCCC(=O)OC)(C(=O)OCC)S(C)(=O)=O)OC(C)=O
ethyl 2-(6-methoxycarbonyl-2-hexyn-1-yl)-2-(4-acetoxynonyl)-2-(methylsulfonyl)-acetate
[Cl-].[Na+]
sodium chloride
→
CCCCCC(O)CCCC(CC#CCCCC(=O)O)S(C)(=O)=O
title compound
CCCCCC(O)CCCC(CC#CCCCC(=O)O)S(C)(=O)=O
8-methylsulfonyl-12-hydroxy-5-heptadecynoic acid

Edukte

O=C=O
carbon dioxide
CCCCCC(CCCC(CC#CCCCC(=O)OC)(C(=O)OCC)S(C)(=O)=O)OC(C)=O
ethyl 2-(6-methoxycarbonyl-2-hexyn-1-yl)-2-(4-acetoxynonyl)-2-(methylsulfonyl)-acetate
[Cl-].[Na+]
sodium chloride

Reagenzien

Keine

Lösungsmittel

CCOCC
ether
CS(C)=O
dimethyl sulfoxide
O
water
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture is cooled
  2. 2
    workup.ADDITIONtreated with 400 ml
  3. 3
    Waschenwashed with water
  4. 4
    Trocknendried over sodium sulfate
  5. 5
    SonstigeEvaporation of the ether in vacuo

Vorschrift

A solution of ethyl 2-(6-methoxycarbonyl-2-hexyn-1-yl)-2-(4-acetoxynonyl)-2-(methylsulfonyl)-acetate (48.8 g., 0.1 mole), water (3.6 g., 0.2 mole), and sodium chloride (6.5 g., 0.11 mole) in 120 ml. of dimethyl sulfoxide is heated at 130°-150° C. for 6 hours until evolution of carbon dioxide is completed. The mixture is cooled, treated with 400 ml. of water and the oily product taken up in ether, washed with water and dried over sodium sulfate. Evaporation of the ether in vacuo leaves the title compound as a yellow viscous oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04128564uspto-grants-1978_12