Dimethylformamide → 1,3-Benzodioxole, 5-methoxy-

HRID 1602893Notes

Reaction equation

HRID 1602893 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.[H-].[Na+].[CH3:13]N(C=O)C>>[CH3:13][O:10][C:7]1[CH:8]=[CH:9][C:3]2[O:2][CH2:1][O:5][C:4]=2[CH:6]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 68289Sesamol

Product 1

HCID 5924531,3-Benzodioxole, 5-methoxy-Yield 96%

Procedure

To a solution of sesamol (10.0 g, 0.072 mol) in DMF (50 ml) was added sodium hydride (2.08 g, 0.087 mol) at room temperature under argon. After stirring for 1 h, the mixture was treated with iodometharc (13.5 ml. 0.216 mol) and stirred for another 18 h. Upon the removal of the solvent the residue was extracted with ethyl acetate and washed with water, dried (Na2SO4) and concentrated to afford the title compound as a dark brown oil (10.5 g, 96%).

Workup

  1. additionthe mixture was treated with iodometharc (13.5 ml. 0.216 mol)
  2. stirringstirred for another 18 h
  3. customUpon the removal of the solvent the residue
  4. extractionwas extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6b6496dceb7c4995b59f330166aa6464
Source dataset
uspto-grants-1999_11
Patent number
US05985886

Reaction notes

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