反应 #710507

反应方程式

NH4Cl

2-adamantone

CH3Li

→

56

收率 95.0%

2-methyl-2-adamantol

收率 95.0%

溶剂

ether

反应条件

后处理

1. 1
   其他brought to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   萃取extracted with ether for three times
4. 4
   干燥The combined ether was dried over MgSO4
5. 5
   浓缩concentrated in vacuo
6. 6
   其他The crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2)

实验过程

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.

来源