Reaktion #710507

Reaktionsgleichung

NH4Cl

2-adamantone

CH3Li

→

56

Ausbeute 95.0%

2-methyl-2-adamantol

Ausbeute 95.0%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigebrought to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   Extraktionextracted with ether for three times
4. 4
   TrocknenThe combined ether was dried over MgSO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2)

Vorschrift

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.

Quelle