Ammonium Chloride → 2-Methyl-2-adamantanol

HRID 623325

Reaction equation

HRID 623325 reaction equation
[CH2:1]1[CH:6]2[CH2:7][CH:8]3[C:10](=[O:11])[CH:4]([CH2:5]2)[CH2:3][CH:2]1[CH2:9]3.[CH3:12][Li].[NH4+].[Cl-]>CCOCC>[CH3:12][C:10]1([OH:11])[CH:4]2[CH2:5][CH:6]3[CH2:1][CH:2]([CH2:3]2)[CH2:9][CH:8]1[CH2:7]3

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 64151AdamantanoneHCID 178418348HCID 178418348, compound

Product 1

HCID 1365452-Methyl-2-adamantanolYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

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.

Workup

  1. custombrought to ambient temperature
  2. stirringstirred overnight
  3. extractionextracted with ether for three times
  4. dry with materialThe combined ether was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was separated by flash column chromatography (CH2Cl2 to 5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-f7715c6b42eb4e2cb15b5435ca246d2a
Source dataset
uspto-grants-2016_04
Patent number
US09301950B2

Linked notes

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