تفاعل #710507

معادلة التفاعل

NH4Cl

2-adamantone

CH3Li

→

56

المردود 95.0%

2-methyl-2-adamantol

المردود 95.0%

المذيبات

ether

ظروف التفاعل

المعالجة

1. 1
   أخرىbrought to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   استخلاصextracted with ether for three times
4. 4
   تجفيفThe combined ether was dried over MgSO4
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2)

الإجراء التجريبي

To a solution of 2-adamantone (1.50 g, 10 mmol) in ether was added CH3Li (7.5 ml, 1.6M in ether, 12 mmol) dropwise at 0° C. under a N2 atmosphere. The mixture was stirred for another hr at 0° C., then brought to ambient temperature and stirred overnight. Saturated NH4Cl solution was added and extracted with ether for three times. The combined ether was dried over MgSO4 and concentrated in vacuo. The crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2) to give 56 as white solid (1.58 g, 95%). 1H-NMR (360 MHz, CDCl3) δ 2.20-2.16 (m, 2H), 1.89-1.75 (m, 6H), 1.68 (br s, 4H), 1.57-1.54 (m, 2H), 1.48 (br s, 1H), 1.35 (s, 3H); 13C-NMR (90 MHz, CDCl3) δ 74.06, 39.30, 38.49, 35.33, 33.16, 27.73, 27.60, 27.22; ESI-MS: Calculated for C11H18O (M+H)+ 167.3. Found: 167.3.

المصدر