Methyl iodide → 5-Methoxyadamantan-2-one

HRID 266040

Reaction equation

HRID 266040 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.O[C:7]12[CH2:16]C3CC([CH2:15][CH:9]([C:10]3=[O:17])[CH2:8]1)[CH2:14]2.CI.[H-].[Na+]>O>[CH3:3][O:4][C:5]12[CH2:1][CH:2]3[CH2:14][CH:7]([CH2:8][CH:9]([C:10]3=[O:17])[CH2:15]1)[CH2:16]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 64184Idramantone

Product 1

HCID 5283525-Methoxyadamantan-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

THF 5 ml solution of 5-hydroxy-2-adamantanone 100 mg and methyl iodide 0.113 ml was cooled at 0° C., and sodium hydride (60%, oil suspension) 48.2 mg was added therein, and the temperature of the reaction mixture was gradually changed to room temperature, then stirred for 25 hours. The reaction mixture was cooled again, and water was added thereto, then THF was removed by concentration in vacuo. The thus obtained residue was extracted with chloroform and dried by adding anhydrous sodium sulfate. After separation of the drying agent, the filtrate was concentrated in vacuo. Residue was purified by means of silica gel column chromatography (Wako gel, C200, n-hexane: ethyl acetate=10:1) to obtain the product.

Workup

  1. customwas gradually changed to room temperature
  2. temperatureThe reaction mixture was cooled again
  3. customTHF was removed by concentration in vacuo
  4. extractionThe thus obtained residue was extracted with chloroform
  5. customdried
  6. additionby adding anhydrous sodium sulfate
  7. customAfter separation of the drying agent
  8. concentrationthe filtrate was concentrated in vacuo
  9. customResidue was purified by means of silica gel column chromatography (Wako gel, C200, n-hexane: ethyl acetate=10:1)
  10. customto obtain the product

Sources & evidence

ORD record
ord-1f05df81ea684a0eac2c1f6724f77769
Source dataset
uspto-grants-1997_07
Patent number
US05650406

Linked notes

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