Methyl iodide → HCID 57263638, compound

HRID 2399567Notes

Reaction equation

HRID 2399567 reaction equation
[OH:1][C@H:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][C@@H:4]([C:10]([CH3:12])=[CH2:11])[C@@H:3]1[C:13]([O:15][CH3:16])=[O:14].[H-].[Na+].[CH3:19]I>CN(C)C=O>[CH3:19][O:1][C@H:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][C@@H:4]([C:10]([CH3:12])=[CH2:11])[C@@H:3]1[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57050928HCID 57050928, compound

Product 1

HCID 57263638HCID 57263638, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the above alcohol (1.15 g) and sodium hydride (230 mg, 60% dispersion in oil) and methyl iodide (0.6 ml) in dry N,N-dimethylformamide was stirred for 3 hrs at room temperature. The mixture was cooled to 0° C., and reaction was quenched by addition of water. The pH of the mixture was adjusted to pH 7 with 0.1N hydrochloric acid. The mixture was extracted with diethyl ether, and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give methyl (1S,2R,6R)-2-methoxy-3,3-dimethyl-6-(1-methylvinyl)-cyclohexane-1-carboxylate (1.12 g, 92% yield).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customreaction
  3. customwas quenched by addition of water
  4. extractionThe mixture was extracted with diethyl ether
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6d76809ec09744bca8f8ad17ea08ea1f
Source dataset
uspto-grants-1995_09
Patent number
US05449785

Reaction notes

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