Reaktion #6568

Reaktionsgleichung

Tris(dimethylamino)phosphine

dibromodifluoromethane

benzyl 7-oxooctanoate

→

Benzyl 8,8-difluoro-7-methyl-7-octenoate

Lösungsmittel

diglyme

diglyme

diglyme

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe ice bath was removed
2. 2
   workup.STIRRINGthe reaction mixture stirred for 40 minutes at room temperature
3. 3
   workup.ADDITIONpoured into 1 liter ice-water
4. 4
   Extraktionextracted with ether
5. 5
   WaschenThe ether phase was washed twice with water
6. 6
   Trocknendried over sodium sulphate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was purified by column chromatography (silica gel hexane/ether=3:1)

Vorschrift

123 ml (0.68 mol) Tris(dimethylamino)phosphine in 100 ml diglyme was added slowly dropwise to a solution of 26.3 ml (0.34 mol) dibromodifluoromethane in 800 ml diglyme. After stirring for one hour on an ice bath, 43 g (0.17 mol}benzyl 7-oxooctanoate in 100 ml diglyme was slowly added dropwise. The ice bath was removed and the reaction mixture stirred for 40 minutes at room temperature, poured into 1 liter ice-water and extracted with ether. The ether phase was washed twice with water, dried over sodium sulphate, filtered and concentrated. The residue was purified by column chromatography (silica gel hexane/ether=3:1)

Quelle