Reaction #70446

Reaction equation

sodium borohydride

3-benzyloxy-2,5-dibromopyridine

n-butyllithium

ammonium chloride

N,N-dimethylformamide

→

title compound

Yield 62.0%

(3-Benzyloxy-5-bromopyridin-2-yl)methanol

Yield 62.0%

Solvents

methanol

toluene

Conditions

Workup

1. 1
   TemperatureAfter gradually warming to room temperature
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 30 minutes, to which
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe organic layer was washed with brine
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Procedure

A solution of 3-benzyloxy-2,5-dibromopyridine (210 mg, 0.612 mmol) in toluene was cooled to −78° C. under N2 and n-butyllithium (1.60M, 0.46 mL, 0.735 mmol) was added dropwise. The mixture was stirred at −78° C. for 2.5 hours followed by the addition of dry N,N-dimethylformamide (0.095 mL, 1.22 mmol). After gradually warming to room temperature, methanol (5 mL) and sodium borohydride (23 mg, 0.612 mmol) was added to the mixture. The resulting mixture was stirred for 30 minutes, to which was added saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give the title compound as a yellow crystal (111 mg, yield 62%).

Source