반응 #710507

반응 방정식

NH4Cl

2-adamantone

CH3Li

→

56

수율 95.0%

2-methyl-2-adamantol

수율 95.0%

용매

ether

반응 조건

후처리

1. 1
   기타brought to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   추출extracted with ether for three times
4. 4
   건조The combined ether was dried over MgSO4
5. 5
   농축concentrated in vacuo
6. 6
   기타The crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2)

실험 절차

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.

출처