Reacción #93919

Ecuación de reacción

ethyl 8-(2-chloroethylsulfonyl)-12-acetoxyheptadecanoate

sodium hydroxide

water

→

title compound

8-vinylsulfonyl-12-hydroxyheptadecanoic acid

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroMost of the tetrahydrofuran is removed by evaporation in vacuo
2. 2
   Otroat 30° C. or below
3. 3
   workup.ADDITIONThe residue is diluted with water (300 ml.)
4. 4
   Extracciónextracted with ether
5. 5
   Lavadowashed with water
6. 6
   Secadodried over sodium sulfate
7. 7
   OtroThe ether is evaporated
8. 8
   Otroto leave the product as a yellowish, very viscous oil
9. 9
   OtroPurification
10. 10
    Lavadoas eluting solvent mixture

Procedimiento

A mixture of ethyl 8-(2-chloroethylsulfonyl)-12-acetoxyheptadecanoate (43.5 g., 0.09 mole), sodium hydroxide (14.4 g., 0.36 mole), water (150 ml.) and tetrahydrofuran (600 ml.) is stirred at 25° C. for 24 hours. Most of the tetrahydrofuran is removed by evaporation in vacuo keeping the temperature of the evaporating solution at 30° C. or below. The residue is diluted with water (300 ml.) and extracted with ether. The aqueous solution is acidified with dilute hydrochloric acid. The oily product is taken up in ether, washed with water and dried over sodium sulfate. The ether is evaporated to leave the product as a yellowish, very viscous oil. Purification is effected by column chromatography on silica gel with benzene-dioxane as eluting solvent mixture. The title compound is obtained as a colorless viscous oil.

Fuente