反応 #58893

反応方程式

HCl

[2-(4-bromo-2-[1,3]dioxan-2-yl-phenoxy)-ethyl]-dimethyl-amine

n-BuLi

Na2CO3

triisopropyl borate

→

4-(2-Dimethylamino-ethoxy)-3-formyl-benzeneboronic acid

溶媒

THF

反応条件

後処理

1. 1
   workup.WAITwas left for an additional, hour
2. 2
   抽出was extracted with EtOAc
3. 3
   洗浄The organic phase was washed with water
4. 4
   乾燥dried (Na2SO4)
5. 5
   その他evaporated in vacuo
6. 6
   workup.ADDITIONAddition of EtOAc afforded beige crystals that
7. 7
   ろ過was filtered of and
8. 8
   その他was used without further purification

実験手順

A stirred solution of [2-(4-bromo-2-[1,3]dioxan-2-yl-phenoxy)-ethyl]-dimethyl-amine (15 mmol) in dry THF (100 mL) was cooled to −78° C. and added n-BuLi (16.5 mmol) dropwise. The reaction was left for 30 min at −78° C. and added triisopropyl borate (22.5 mmol). The reaction was heated to room temperature, was added 2M HCl (aq, 50 mL) and was left for an additional, hour. The mixture was added 1M Na2CO3 to neutral pH and was extracted with EtOAc. The organic phase was washed with water, dried (Na2SO4) and evaporated in vacuo. Addition of EtOAc afforded beige crystals that was filtered of and was used without further purification.

出典