反応 #736551

反応方程式

hydrochloride

N-methylbenzylamine

ethyl 4-(chlorocarbonyloxy)-2-butynoate

→

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

収率 28.6%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONwas rapidly added
2. 2
   温度under cooling with ice
3. 3
   その他The mixture was reacted for 1 hour
4. 4
   温度cooling with ice
5. 5
   抽出subjected to extraction treatment
6. 6
   抽出The dichloromethane extraction solution
7. 7
   乾燥was dried over sodium sulfate
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他The residue was purified by silica gel column chromatography (with use of 30 g of silica gel)
10. 10
    洗浄The desired fraction eluted by hexane-benzene (1:0→3:1)
11. 11
    その他was collected
12. 12
    濃縮concentrated under reduced pressure

実験手順

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.

出典