반응 #564626

반응 방정식

phosphorous pentachloride

α-[(2,2-dimethylpropoxy)methyl]-1-pyrrolidineethanol

potassium hydroxide

→

oil

수율 72.1%

1-[2-Chloro-3-(2,2-dimethylpropoxy)propyl]pyrrolidine

수율 72.1%

용매

toluene

toluene

반응 조건

후처리

1. 1
   기타Dry hydrogen chloride gas was bubbled into an ice-
2. 2
   온도cooled
3. 3
   기타between 10°-15° C
4. 4
   workup.ADDITIONAfter the addition
5. 5
   기타the ice bath was removed
6. 6
   workup.ADDITIONThe reaction mixture was added to a stirred ice-
7. 7
   기타between 25°-35° C
8. 8
   workup.STIRRINGThe reaction mixture was stirred for 0.5 hr
9. 9
   추출then extracted with toluene
10. 10
    기타An immiscible oil formed between the layers
11. 11
    기타The oil was partitioned between dichloromethane and water
12. 12
    기타dried
13. 13
    농축concentrated to dryness

실험 절차

Dry hydrogen chloride gas was bubbled into an ice-cooled solution of 107.7 g (0.5 mole) of α-[(2,2-dimethylpropoxy)methyl]-1-pyrrolidineethanol (the product of Example 3a) in 110 ml of dry toluene until 20.05 g (0.55 mole) was taken up. This solution was added to a stirred ice-cooled suspension of 109.4 g (0.525 mole) of phosphorous pentachloride in 60ml of dry toluene (argon atmosphere) at a rate to keep the reaction temperature between 10°-15° C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred for 1.5 hr. The reaction mixture was added to a stirred ice-cooled solution of 385 ml (4.5 mole) of 45% potassium hydroxide and 700 ml of ice at a rate to keep the reaction temperature between 25°-35° C. The reaction mixture was stirred for 0.5 hr then extracted with toluene. An immiscible oil formed between the layers. The oil was partitioned between dichloromethane and water. The dichloromethane layer and the toluene layer above were combined, dried and concentrated to dryness to give 84.3 g of oil. The oil was distilled (65°-86° C. at 0.35 mm) to give 76.63 g of oily product.

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