Reacción #2304289

Ecuación de reacción

3-ethyl-3-hydroxymethyloxetane

p-toluenesulfonyl chloride

→

3-[(tosyloxy)methyl]-3-ethyloxetane

Rendimiento 90.2%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to it intermittently
2. 2
   workup.STIRRINGKept at 0° C., this was stirred for 5 hours
3. 3
   ExtracciónThis was extracted with 500 ml of diethyl ether
4. 4
   LavadoThe diethyl ether layer was washed with 3% hydrochloric acid until its pH
5. 5
   Lavadowashed with saturated sodium carbonate solution and water in this order
6. 6
   Secadodried with anhydrous magnesium sulfate
7. 7
   OtroThe solvent was evaporated away

Procedimiento

116 g of 3-ethyl-3-hydroxymethyloxetane (Toa Gosei's trade name, OXT-101) was added to 500 ml of pyridine, and cooled to 0° C. with stirring. 190 g of p-toluenesulfonyl chloride divided into a few portions was added to it intermittently. Kept at 0° C., this was stirred for 5 hours, and then 1 L of ice-water was poured into the reaction mixture. This was extracted with 500 ml of diethyl ether. The diethyl ether layer was washed with 3% hydrochloric acid until its pH became acidic, and then washed with saturated sodium carbonate solution and water in this order, and thereafter dried with anhydrous magnesium sulfate. The solvent was evaporated away, and 243 g of 3-[(tosyloxy)methyl]-3-ethyloxetane was obtained.

Fuente