반응 #1463494

반응 방정식

5-hexyn-1-ol

pyridine

Tosyl chloride

→

1-tosyloxyhex-5-yne

용매

dichloromethane

반응 조건

후처리

1. 1
   기타the reaction was transferred to a separating funnel
2. 2
   세척washed with 2N HCl (2×50 ml) and saturated sodium bicarbonate (2×50 ml)
3. 3
   추출These were back extracted with dichloromethane (1×25 ml)
4. 4
   세척the combined organic layers washed with water (1×50 ml)
5. 5
   건조After drying (Na2SO4)
6. 6
   여과the liquid was filtered off
7. 7
   기타the solvent evaporated
8. 8
   기타to leave the product--33.4 g (93%)

실험 절차

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.

출처