반응 #58893

반응 방정식

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

용매

THF

반응 조건

후처리

1. 1
   workup.WAITwas left for an additional, hour
2. 2
   추출was extracted with EtOAc
3. 3
   세척The organic phase was washed with water
4. 4
   건조dried (Na2SO4)
5. 5
   기타evaporated in vacuo
6. 6
   workup.ADDITIONAddition of EtOAc afforded beige crystals that
7. 7
   여과was filtered of and
8. 8
   기타was used without further purification

실험 절차

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.

출처