反応 #417947

反応方程式

benzyl chloroformate

4-(1-amino-ethyl)-phenol hydrobromide

THF

NaHCO3

→

(S)-Benzyl 1-(4-hydroxyphenyl)ethylcarbamate

溶媒

H2O

反応条件

後処理

1. 1
   workup.ADDITIONare added
2. 2
   その他Afterwards the reaction mixture is quenched by the addition of water
3. 3
   抽出Then the product is extracted with EtOAc
4. 4
   乾燥the combined organic layers are dried over MgSO4
5. 5
   ろ過filtered
6. 6
   その他the solvent is removed in vacuo
7. 7
   その他The crude product is purified by flash chromatography (silica gel, PE/EtOAc)

実験手順

5.00 g (22.9 mmol) 4-(1-amino-ethyl)-phenol hydrobromide are added to 10 mL THF and 10 mL H2O before 13.5 g (160 mmol) NaHCO3 are added. Then 3.60 mL (25.2 mmol) benzyl chloroformate are added dropwise and the reaction mixture is stirred at r.t. for 3 h. Afterwards the reaction mixture is quenched by the addition of water and is set to a gentle acidic pH value using citric acid (10% in water). Then the product is extracted with EtOAc, the combined organic layers are dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by flash chromatography (silica gel, PE/EtOAc).

出典