Reaction #710507

Reaction equation

NH4Cl

2-adamantone

CH3Li

→

56

Yield 95.0%

2-methyl-2-adamantol

Yield 95.0%

Solvents

ether

Conditions

Workup

1. 1
   Otherbrought to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   Extractionextracted with ether for three times
4. 4
   DryingThe combined ether was dried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2)

Procedure

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.

Source