反応 #710507

反応方程式

NH4Cl

2-adamantone

CH3Li

→

56

収率 95.0%

2-methyl-2-adamantol

収率 95.0%

溶媒

ether

反応条件

後処理

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

実験手順

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.

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