تفاعل #414185

معادلة التفاعل

diethyl P-(hydroxymethyl)phosphonate

triethylamine

ether

2-(trifluoromethyl)benzenesulfonyl chloride

ether

→

desired product

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

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe addition
2. 2
   أخرىto form shortly
3. 3
   workup.ADDITIONafter the addition
4. 4
   غسيلwashed with three 85 ml portions of water
5. 5
   تجفيفThe organic phase was dried with magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىThe resulting crude product was purified via flash chromatography on Merck® silica gel (230-400 mesh)
9. 9
   غسيلeluting with hexanes and ethyl acetate

الإجراء التجريبي

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.

المصدر