反応 #70446

反応方程式

sodium borohydride

3-benzyloxy-2,5-dibromopyridine

n-butyllithium

ammonium chloride

N,N-dimethylformamide

→

title compound

収率 62.0%

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

収率 62.0%

溶媒

methanol

toluene

反応条件

後処理

1. 1
   温度After gradually warming to room temperature
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 30 minutes, to which
3. 3
   抽出extracted with ethyl acetate
4. 4
   洗浄The organic layer was washed with brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

実験手順

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%).

出典