反応 #160765

反応方程式

4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine

NBS

ethyl acetate

→

(+/−)-6-bromo-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol

収率 80.0%

溶媒

THF

water

water

反応条件

後処理

1. 1
   乾燥the organic phase was dried with brine
2. 2
   ろ過sodium sulfate, filtered
3. 3
   濃縮concentrated
4. 4
   その他The crude material was purified via silica gel column chromatography
5. 5
   洗浄eluting with ethyl acetate and hexanes (1:1)

実験手順

To a solution of 4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine (1.0 equiv.) in THF and water (1:1, 0.13M) was added NBS (1.5 equiv.) and the reaction was stirred at room temperature for 30 min. Upon completion, ethyl acetate and water were added to the reaction, the organic phase was dried with brine, then sodium sulfate, filtered, and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:1) to give (+/−)-6-bromo-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol as a yellow oil in 80% yield. LC/MS=315.0/313.0 (M+H), LC=2.966 min.

出典