反応 #485248

反応方程式

4-bromomethyl-2,6-di-t-butylpyridine

4-bromomethyl-2,6-di-tert-butylpyridine

Compound A3

4-bromomethyl-2,6-di-tert-butylpyridine

1,4-dioxane

→

4-Hydroxymethyl-2,6-di-t-butylpyridine

溶媒

NaOH

water

反応条件

後処理

1. 1
   その他The solution spontaneously separated into two layers as it
2. 2
   その他The upper layer was separated
3. 3
   workup.ADDITIONethyl acetate was added
4. 4
   洗浄This organic layer was then washed with brine, water
5. 5
   乾燥dried over MgSO4
6. 6
   その他The desired product was purified by column chromatography (ethyl acetate/hexane 1/9)
7. 7
   その他to give a white solid

実験手順

A heterogeneous solution of 4-bromomethyl-2,6-di-t-butylpyridine (Compound A3, 1.743 g, 82% purity) in 20 ml of 12% NaOH in water and 10 ml of 1,4-dioxane was refluxed for 12 hours. The solution spontaneously separated into two layers as it cooled to room temperature. The upper layer was separated and ethyl acetate was added. This organic layer was then washed with brine, water and dried over MgSO4. The desired product was purified by column chromatography (ethyl acetate/hexane 1/9) to give a white solid. 1H NMR δ7.09 (s, 2H), 4.67 (d, J=4.4 Hz, 2H), 2.3 (b, 1H), 1.36 (s, 18H).

出典