Reacción #1463494

Ecuación de reacción

5-hexyn-1-ol

pyridine

Tosyl chloride

→

1-tosyloxyhex-5-yne

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction was transferred to a separating funnel
2. 2
   Lavadowashed with 2N HCl (2×50 ml) and saturated sodium bicarbonate (2×50 ml)
3. 3
   ExtracciónThese were back extracted with dichloromethane (1×25 ml)
4. 4
   Lavadothe combined organic layers washed with water (1×50 ml)
5. 5
   SecadoAfter drying (Na2SO4)
6. 6
   Filtraciónthe liquid was filtered off
7. 7
   Otrothe solvent evaporated
8. 8
   Otroto leave the product--33.4 g (93%)

Procedimiento

5-hexyn-1-ol (14 g), pyridine (20 ml) and dichloromethane (60 ml) were mixed and cooled to 0° C. Tosyl chloride (30 g:1.1 equivalent) was added portion wise over 20 minutes. After 5 hours at 0° C., the reaction was transferred to a separating funnel and washed with 2N HCl (2×50 ml) and saturated sodium bicarbonate (2×50 ml). These were back extracted with dichloromethane (1×25 ml) and the combined organic layers washed with water (1×50 ml). After drying (Na2SO4), the liquid was filtered off and the solvent evaporated to leave the product--33.4 g (93%)--of sufficient purity to be used for the next step.

Fuente