Methyl iodide → 6-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine

HRID 428149Notes

Reaction equation

HRID 428149 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[H-].[Na+].I[CH3:15]>CN(C=O)C>[CH3:15][O:11][C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 91152732,3-Dihydro-1,4-benzodioxin-6-ol

Product 1

HCID 109099186-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g (18.05 mmol) of the alcohol obtained in Step A are dissolved in 10 ml of DMF in a flask. 2 eq. of NaH (60% in oil) are added slowly and allowed to act for 30 minutes under an inert atmosphere. 2 eq. of iodomethane are then added. The mixture is stirred for 2 hours; the DMF is then evaporated. Washing with ethyl acetate and with water is carried out and the two phases are separated. The combined organic phases are dried over MgSO4 and the solvent is evaporated. The oil obtained is purified on a silica column (eluant: PE/AcOEt 8/2), which allows the pure title product to be obtained.

Workup

  1. customthe DMF is then evaporated
  2. washWashing with ethyl acetate and with water
  3. customthe two phases are separated
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. customthe solvent is evaporated
  6. customThe oil obtained
  7. customis purified on a silica column (eluant: PE/AcOEt 8/2), which
  8. customto be obtained

Sources & evidence

ORD record
ord-235576a5bb8949a69272b238d622c72f
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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