Reaction #710506

Reaction equation

Water

1-adamantanemethanol

PCC

→

49

Yield 83.0%

1-adamantanecarboaldehyde

Yield 83.0%

Solvents

CH2Cl2

Conditions

Workup

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

Procedure

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.

Source