Reacción #710507

Ecuación de reacción

NH4Cl

2-adamantone

CH3Li

→

56

Rendimiento 95.0%

2-methyl-2-adamantol

Rendimiento 95.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrobrought to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   Extracciónextracted with ether for three times
4. 4
   SecadoThe combined ether was dried over MgSO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2)

Procedimiento

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.

Fuente