Reaktion #414192

Reaktionsgleichung

triethylamine

2-(trifluoromethyl)benzenesulfonyl chloride

O-ethyl P-methyl(hydroxymethyl)phosphinate

triethylamine

→

desired product

Ausbeute 14.5%

O-Ethyl P-methyl[[(2-(trifluoromethyl)phenyl)sulfonyloxy]methyl]phosphinate

Ausbeute 14.5%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto form shortly
2. 2
   EinengenThe reaction mixture was concentrated
3. 3
   Sonstigethe concentrate was partitioned between 220 ml of ethyl acetate and 50 ml of water
4. 4
   WaschenThe organic phase was washed with an additional 50 ml of water
5. 5
   Trocknendried with magnesium sulfate, gravity
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto yield an orange solid
9. 9
   Sonstigechromatographed on silica gel

Vorschrift

A solution of 8 ml of triethylamine diluted with 25 ml of THF was slowly added dropwise over two hours to a mixture of 11.2 g of 2-(trifluoromethyl)benzenesulfonyl chloride, 6.05 g of O-ethyl P-methyl(hydroxymethyl)phosphinate, (Example 22, Method B), and 60 ml of THF. A white precipitate began to form shortly after the addition of the triethylamine solution was begun. No significant exotherm occurred and the reaction was allowed to stir overnight. The reaction mixture was concentrated and the concentrate was partitioned between 220 ml of ethyl acetate and 50 ml of water. The organic phase was washed with an additional 50 ml of water, dried with magnesium sulfate, gravity filtered, and concentrated to yield an orange solid. The solid was flash chromatographed on silica gel using ethyl acetate to yield 2.2 g of the desired product, melting point 91°-92.5° C.

Quelle