Methyl iodide → 7-Methoxy-2-methoxy-methylbenzofuran

HRID 1282027Notes

Reaction equation

HRID 1282027 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:13]2[O:12][C:11](CO)=[CH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.I[CH3:17].[O:18]1CCC[CH2:19]1>>[CH3:3][O:4][C:5]1[C:13]2[O:12][C:11]([O:18][CH3:19])=[C:10]([CH3:17])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11788606(7-Methoxy-1-benzofuran-2-yl)methanol

Product 1

HCID 701441707-Methoxy-2-methoxy-methylbenzofuran

Procedure

Sodium hydride (3.82 g, 60% in mineral oil) was added to a solution of 7-methoxy-benzofuran-2-ylmethanol (11.21 g) in dry tetrahydrofuran (300 ml) under an atmosphere of dry nitrogen at room temperature. After 10 minutes iodomethane (15.67 ml) was added and the reaction was left to stir overnight. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (100 ml) and water (50 ml). The organic extract was washed with water (50 ml), followed by brine (50 ml), dried over magnesium sulphate, filtered and the solvent removed in vacuo to afford the title compound (13.32 g) as a yellow oil.

Workup

  1. waitthe reaction was left
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate (100 ml) and water (50 ml)
  4. extractionThe organic extract
  5. washwas washed with water (50 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-952849ad235d460aa91f7cd0e23da08e
Source dataset
uspto-grants-2002_09
Patent number
US06455561B1

Reaction notes

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