Dimethylformamide → HCID 67244819, compound

HRID 1519716Notes

Reaction equation

HRID 1519716 reaction equation
IC.CN([CH:6]=[O:7])C.[Br:8][C:9]1[CH:10]=[C:11]([CH2:14]O)[O:12][CH:13]=1.[H-].[Na+]>O.C(OCC)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH2:14][O:7][CH3:6])[O:12][CH:13]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12289784(4-Bromofuran-2-yl)methanol

Product 1

HCID 67244819HCID 67244819, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodomethane (1.6 mL) was added to a DMF (15 mL) solution of (4-bromofuran-2-yl)methanol (3.0 g) as obtained in Example 18-(1). Under ice cooling, 60% sodium hydride (0.82 g) was added in divided portions, and the mixture was stirred for 1 hour and 40 minutes at room temperature. Ethyl acetate and water were added, and the organic layer was isolated. The extract was washed with water and brine sequentially, and dried over anhydrous magnesium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure to obtain partially purified 4-bromo-2-(methoxymethyl)furan (yellow oil) (3.9 g).

Workup

  1. customas obtained in Example 18-(1)
  2. customthe organic layer was isolated
  3. washThe extract was washed with water and brine sequentially
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThen, the desiccant was filtered out
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9d2f670a34704710a4ac0d3cfa36bbdc
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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