Реакция #710507

Уравнение реакции

NH4Cl

2-adamantone

CH3Li

→

56

Выход 95.0%

2-methyl-2-adamantol

Выход 95.0%

Растворители

ether

Условия реакции

Обработка

1. 1
   Другоеbrought to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   Экстракцияextracted with ether for three times
4. 4
   СушкаThe combined ether was dried over MgSO4
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2)

Методика

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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