Reaktion #58893

Reaktionsgleichung

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITwas left for an additional, hour
2. 2
   Extraktionwas extracted with EtOAc
3. 3
   WaschenThe organic phase was washed with water
4. 4
   Trocknendried (Na2SO4)
5. 5
   Sonstigeevaporated in vacuo
6. 6
   workup.ADDITIONAddition of EtOAc afforded beige crystals that
7. 7
   Filtrationwas filtered of and
8. 8
   Sonstigewas used without further purification

Vorschrift

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.

Quelle