Methyl iodide → 2-(Cyclopropyl-methoxy-methyl)-7-methoxybenzofuran

HRID 1108299Notes

Reaction equation

HRID 1108299 reaction equation
[H-].[Na+].[CH:3]1([CH:6]([C:8]2[O:9][C:10]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)[OH:7])[CH2:5][CH2:4]1.I[CH3:20]>O1CCCC1>[CH:3]1([CH:6]([O:7][CH3:20])[C:8]2[O:9][C:10]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18784867Cyclopropyl-(7-methoxybenzofuran-2-yl)-methanol

Product 1

HCID 187848602-(Cyclopropyl-methoxy-methyl)-7-methoxybenzofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of sodium hydride (60% dispersion in mineral oil, 0.52 g) in tetrahydrofuran (60 ml) under an atmosphere of nitrogen was added slowly a solution of cyclopropyl-(7-methoxybenzofuran-2-yl)-methanol (1.88 g) in tetrahydrofuran (15 ml). After stirring for 5 minutes, iodomethane (1.6 ml) was added and the mixture concentrated in vacuo. The residue was partitioned between ethyl acetate (100 ml) and water (100 ml), the organic layer washed with water (100 ml), separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with dichloromethane afforded the title compound as a yellow gum (1.62 g).

Workup

  1. concentrationthe mixture concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. washthe organic layer washed with water (100 ml)
  4. customseparated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica eluting with dichloromethane

Sources & evidence

ORD record
ord-6db5ecc150054891ad615a26161b92a0
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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