Methyl iodide → HCID 19392462, compound

HRID 37163Notes

Reaction equation

HRID 37163 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[O:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][O:9][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:18]I>CN(C)C=O>[CH3:18][O:1][C:2]1[CH:15]=[CH:14][C:5]2[O:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19392464Methyl 6-hydroxy-1,4-benzodioxin-2-carboxylate

Product 1

HCID 19392462HCID 19392462, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir for 15 minutes at room temperature, under argon, a solution of 0.48 mmol of methyl 6-hydroxy -1,4-benzodioxin-2-carboxylate in 5 cm3 of N,N-dimethylformamide in the presence of 0.57 mmol of 60% sodium hydride suspended in oil, and then add 0.72 mmol of methyl iodide. After being stirred for 4 hours at room temperature, the reaction mixture is concentrated under reduced pressure and then extracted with methylene chloride. After the methylene chloride phases have been concentrated to dryness, the crude product is purified by chromatography on a silica column (eluant:petroleum ether/ethyl acetate, 80:20). Methyl 6-methoxy -1,4-benzodioxin-2-carboxylate is thereby obtained in a yield of 78%.

Workup

  1. stirringAfter being stirred for 4 hours at room temperature
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. extractionextracted with methylene chloride
  4. concentrationAfter the methylene chloride phases have been concentrated to dryness
  5. customthe crude product is purified by chromatography on a silica column (eluant:petroleum ether/ethyl acetate, 80:20)

Sources & evidence

ORD record
ord-f976d273c0ce4b449071e7e2b48000da
Source dataset
uspto-grants-1995_05
Patent number
US05420132

Reaction notes

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