반응 #710506

반응 방정식

Water

1-adamantanemethanol

PCC

→

49

수율 83.0%

1-adamantanecarboaldehyde

수율 83.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for 1.5 hrs until the disappearance of starting material
3. 3
   추출extracted with CH2Cl2 for 3 times
4. 4
   건조The combined organic phase was dried over MgSO4
5. 5
   여과filtrated
6. 6
   농축concentrated in vacuo
7. 7
   기타The crude mixture was separated by flash chromatography (50%-100% CH2Cl2/Hexane)

실험 절차

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.

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