반응 #736551

반응 방정식

hydrochloride

N-methylbenzylamine

ethyl 4-(chlorocarbonyloxy)-2-butynoate

→

ethyl 4-(N-benzyl-N-methylcarbamoyloxy)-2-butynoate

수율 28.6%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas rapidly added
2. 2
   온도under cooling with ice
3. 3
   기타The mixture was reacted for 1 hour
4. 4
   온도cooling with ice
5. 5
   추출subjected to extraction treatment
6. 6
   추출The dichloromethane extraction solution
7. 7
   건조was dried over sodium sulfate
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The residue was purified by silica gel column chromatography (with use of 30 g of silica gel)
10. 10
    세척The desired fraction eluted by hexane-benzene (1:0→3:1)
11. 11
    기타was collected
12. 12
    농축concentrated under reduced pressure

실험 절차

2.85 g (15 millimoles) of ethyl 4-(chlorocarbonyloxy)-2-butynoate obtained in the first step of Example VI-9 was dissolved in 20 ml of dichloromethane, and 9 ml of a dichloromethane solution containing 3.1 ml (24 millimoles) of N-methylbenzylamine was rapidly added under cooling with ice. The mixture was reacted for 1 hour under stirring and cooling with ice. The reaction mixture was poured into ice water, adjusted to pH 2 with dilute hydrochloride acid and subjected to extraction treatment. The dichloromethane extraction solution was dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (with use of 30 g of silica gel). The desired fraction eluted by hexane-benzene (1:0→3:1), was collected and concentrated under reduced pressure, whereby 1.18 g (yield: 28.5%) of colorless oily ethyl 4-(N-benzyl-N-methylcarbamoyloxy)-2-butynoate was obtained.

출처