Reaktion #621085

Reaktionsgleichung

peracetic acid

5-bromo-2-cyclopropoxypyridine

n-BuLi

NaHSO3

trimethylborate

→

subtitle compound

6-Cyclopropoxy-pyridin-3-ol

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise within 10 minutes
2. 2
   ExtraktionThe mixture was extracted with EA
3. 3
   TrocknenThe organic phase was dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by chromatography (silica gel, heptane to EA/heptane 2:3)

Vorschrift

A mixture of 5-bromo-2-cyclopropoxypyridine (Milestone Pharmtech, 500 mg) in THF (10 mL) was cooled (−78° C.) and n-BuLi (2.5 M in toluene, 1.49 mL) was added dropwise within 10 minutes. After 20 minutes trimethylborate (429 μL) was added. After 2 hours peracetic acid (32% in AcOH, 786 μL) was added dropwise. After 10 minutes the reaction temperature was changed to 0° C. After 1 hour the mixture was poured into aqueous NaHSO3-solution (5%, 5 mL). The mixture was extracted with EA. The organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography (silica gel, heptane to EA/heptane 2:3) to provide the subtitle compound. MS ESI+: m/z=152 [M+H]+.

Quelle