Reaktion #414185

Reaktionsgleichung

diethyl P-(hydroxymethyl)phosphonate

triethylamine

ether

2-(trifluoromethyl)benzenesulfonyl chloride

ether

→

desired product

Diethyl P-[[(2-(trifluoromethyl)phenyl)sulfonyloxy]methyl]phosphonate

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe addition
2. 2
   Sonstigeto form shortly
3. 3
   workup.ADDITIONafter the addition
4. 4
   Waschenwashed with three 85 ml portions of water
5. 5
   TrocknenThe organic phase was dried with magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe resulting crude product was purified via flash chromatography on Merck® silica gel (230-400 mesh)
9. 9
   Wascheneluting with hexanes and ethyl acetate

Vorschrift

A solution of 11.1 g of diethyl P-(hydroxymethyl)phosphonate (Example 17), 11 ml of triethylamine and 30 ml of ether was added dropwise over one hour to 15.5 g of 2-(trifluoromethyl)benzenesulfonyl chloride and 50 ml of anhydrous ether. The addition was mildly exothermic and a white precipitate began to form shortly after the addition was begun. The reaction was stirred overnight, then diluted with 300 ml of ethyl acetate and washed with three 85 ml portions of water. The organic phase was dried with magnesium sulfate, filtered and concentrated. The resulting crude product was purified via flash chromatography on Merck® silica gel (230-400 mesh) eluting with hexanes and ethyl acetate to yield 10.5 g of the desired product as an oil.

Quelle