反応 #710506

反応方程式

Water

1-adamantanemethanol

PCC

→

49

収率 83.0%

1-adamantanecarboaldehyde

収率 83.0%

溶媒

CH2Cl2

反応条件

後処理

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

実験手順

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.

出典