Sodium Chloride → 5-Methoxyadamantan-2-one

HRID 2092019

Reaction equation

HRID 2092019 reaction equation
[H-].[Na+].[OH:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([C:7]3=[O:14])[CH2:5]1)[CH2:11]2.[CH3:15]I.[Cl-].[Na+]>CN(C)C=O>[CH3:15][O:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([C:7]3=[O:14])[CH2:5]1)[CH2:11]2

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 64184Idramantone

Product 1

HCID 5283525-Methoxyadamantan-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

55% sodium hydride (40 mg, 0.917 mmol) in N,N-dimethylformamide (1 mL) was mixed with 5-hydroxy-2-adamantanone (100 mg, 0.602 mmol) and methyl iodide (750 μL, 12 mmol) at 0° C. and stirred at 50° C. for 8 hours. After completion of the reaction, the reaction solution was mixed with saturated aqueous sodium chloride and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting crude reaction product containing the desired product was used for the next step.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting crude reaction product

Sources & evidence

ORD record
ord-78cda1bd7ec745ee8df312444fe1eef4
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Linked notes

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