تفاعل #70446

معادلة التفاعل

sodium borohydride

3-benzyloxy-2,5-dibromopyridine

n-butyllithium

ammonium chloride

N,N-dimethylformamide

→

title compound

المردود 62.0%

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

المردود 62.0%

المذيبات

methanol

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter gradually warming to room temperature
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 30 minutes, to which
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   غسيلThe organic layer was washed with brine
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

الإجراء التجريبي

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%).

المصدر