反応 #5105

反応方程式

hydrogen peroxide

5-(p-tert-butylphenoxy)-1-pentene

9-borabicyclononane

sodium hydroxide

→

5-p-t-butylphenoxy-1-pentanol

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度at reflux for one hour
2. 2
   その他was partitioned between 150 ml ether-150 ml water
3. 3
   その他The ether layer was removed
4. 4
   乾燥dried (MgSO4)
5. 5
   その他evaporated to a yellow oil which
6. 6
   その他was chromatographed through 300 g, 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent)
7. 7
   その他yielding a yellow oil which
8. 8
   その他distiled (126° C./0.75 mm) to a clear, colorless oil, 5-p-t-butylphenoxy-1-pentanol, 1.7 g

実験手順

The 5-(p-tert-butylphenoxy)-1-pentene (10.5 g) was treated with 115 ml 0.5M 9-borabicyclononane in tetrahydrofuran and the reaction mixture was stirred at reflux for one hour. The solution was cooled to room temperature and treated with 25 ml 3N sodium hydroxide, then 10 ml 30% hydrogen peroxide. After the bubbling ceased the reaction mixture was partitioned between 150 ml ether-150 ml water. The ether layer was removed, dried (MgSO4), and evaporated to a yellow oil which was chromatographed through 300 g, 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent) yielding a yellow oil which was vacuum distiled (126° C./0.75 mm) to a clear, colorless oil, 5-p-t-butylphenoxy-1-pentanol, 1.7 g.

出典