反应 #710506

反应方程式

Water

1-adamantanemethanol

PCC

→

49

收率 83.0%

1-adamantanecarboaldehyde

收率 83.0%

溶剂

CH2Cl2

反应条件

后处理

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for 1.5 hrs until the disappearance of starting material
3. 3
   萃取extracted with CH2Cl2 for 3 times
4. 4
   干燥The combined organic phase was dried over MgSO4
5. 5
   过滤filtrated
6. 6
   浓缩concentrated in vacuo
7. 7
   其他The crude mixture was separated by flash chromatography (50%-100% CH2Cl2/Hexane)

实验过程

To a solution of 1-adamantanemethanol (1.66 g, 10 mmol) in CH2Cl2 was added PCC (4.3 g, 20 mmol) at 0° C. The resulting mixture was stirred at the same temperature for 10 mins before warming to ambient temperature. Stirring was continued for 1.5 hrs until the disappearance of starting material as checked by TLC. Water was added and extracted with CH2Cl2 for 3 times. The combined organic phase was dried over MgSO4, filtrated and concentrated in vacuo. The crude mixture was separated by flash chromatography (50%-100% CH2Cl2/Hexane) to give 49 as white solid (1.36 g, Yield: 83%). 1H-NMR (360 MHz, CDCl3) δ 9.32 (s, 1H), 2.07 (br s, 3H), 1.77 (br s, 6H), 1.72 (br s, 6H); 13C-NMR (90 MHz, CDCl3) δ 206.07, 45.03, 37.25, 36.10, 27.61; ESI-MS: Calculated for C11H16O (M+H)+ 165.2. Found: 165.5.

来源