Methyl iodide → Methyl 2-methoxy-2-(naphthalen-2-yl)acetate

HRID 388252Notes

Reaction equation

HRID 388252 reaction equation
[OH:1][CH:2]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].CI.[C:21](OCC)(=O)C>CN(C=O)C>[CH3:21][O:1][CH:2]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 53825712Methyl 2-hydroxy-2-(naphthalen-2-yl)acetate

Product 1

HCID 302866Methyl 2-methoxy-2-(naphthalen-2-yl)acetateYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 2-hydroxy-2-(naphthalen-2-yl)acetate (0.63 g, 1 eq) in dry DMF was added NaH (0.45 g, 4 eq) and methyl iodide (0.74 mL, 4.1 eq). Stirring was then continued for 24 hours. The reaction mixture was then poured into ethyl acetate and washed with H2O. The combined organic fractions were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield an oil that was purified by column chromatography using ethyl acetate and hexanes to yield an oil (0.358 g, 53%).

Workup

  1. washwashed with H2O
  2. dry with materialThe combined organic fractions were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield an oil that
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b51556237b0b4d6dab146bb66927285c
Source dataset
uspto-grants-2013_02
Patent number
US08377930B2

Reaction notes

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