تفاعل #93921

ord-542ca5e3dfdf496daa193719263b12ae

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

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

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe mixture is cooled
  2. 2
    workup.ADDITIONtreated with 400 ml
  3. 3
    غسيلwashed with water
  4. 4
    تجفيفdried over sodium sulfate
  5. 5
    أخرىEvaporation of the ether in vacuo

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04128564uspto-grants-1978_12