Reaktion #710506

Reaktionsgleichung

Water

1-adamantanemethanol

PCC

→

49

Ausbeute 83.0%

1-adamantanecarboaldehyde

Ausbeute 83.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle