Reacción #710506

Ecuación de reacción

Water

1-adamantanemethanol

PCC

→

49

Rendimiento 83.0%

1-adamantanecarboaldehyde

Rendimiento 83.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente