تفاعل #710506

معادلة التفاعل

Water

1-adamantanemethanol

PCC

→

49

المردود 83.0%

1-adamantanecarboaldehyde

المردود 83.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر