반응 #70446

반응 방정식

sodium borohydride

3-benzyloxy-2,5-dibromopyridine

n-butyllithium

ammonium chloride

N,N-dimethylformamide

→

title compound

수율 62.0%

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

수율 62.0%

용매

methanol

toluene

반응 조건

후처리

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

실험 절차

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%).

출처