Реакция #710506

Уравнение реакции

Water

1-adamantanemethanol

PCC

→

49

Выход 83.0%

1-adamantanecarboaldehyde

Выход 83.0%

Растворители

CH2Cl2

Условия реакции

Обработка

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

Методика

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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