Reacción #93921

ord-542ca5e3dfdf496daa193719263b12ae

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

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

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe mixture is cooled
  2. 2
    workup.ADDITIONtreated with 400 ml
  3. 3
    Lavadowashed with water
  4. 4
    Secadodried over sodium sulfate
  5. 5
    OtroEvaporation of the ether in vacuo

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04128564uspto-grants-1978_12