반응 #86056

반응 방정식

NCS

dichloromethane

2-propyn-1-ol

Benzaldehyde oxime

dichloromethane

N-chlorosuccinimide

→

3-phenyl-5-hydroxymethyl-isoxazole

수율 76.8%

용매

triethylamine

triethylamine

반응 조건

후처리

1. 1
   workup.DISSOLUTIONwas completely dissolved
2. 2
   workup.ADDITIONAfter the addition
3. 3
   온도the system was refluxed
4. 4
   세척the mother liquor was washed with water
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타was separated on column (Vpetroleum ether:Vethyl acetate=5:1-2:1)

실험 절차

10.0 mmol of Benzaldehyde oxime and 30 ml of dry dichloromethane were added into a 250 ml single-necked round-bottom flask. After the addition of 1.60 g (12.0 mmol) of N-chlorosuccinimide (NCS) under stirring, the mixture was slightly heated until NCS was completely dissolved. 0.56 g (10.0 mmol) of 2-propyn-1-ol was added dropwise, and then 20 ml solution of triethylamine in dichloromethane containing 10.1 g (10.0 mmol) of triethylamine was slowly added dropwise. After the addition was complete, the system was refluxed. After the completion of the reaction monitored by TLC, the mother liquor was washed with water, dried over anhydrous sodium sulfate and was separated on column (Vpetroleum ether:Vethyl acetate=5:1-2:1) to give 3-phenyl-5-hydroxymethyl-isoxazole in 76.8% yield.

출처