Methyl iodide → HCID 22729192, compound

HRID 2221445Notes

Reaction equation

HRID 2221445 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:9]2[CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1.[CH3:17]I>CN(C=O)C>[CH3:17][O:3][C:4]1[C:9]2[CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14494065Methyl 4-hydroxybenzofuran-2-carboxylate

Product 1

HCID 22729192HCID 22729192, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (32.5 mg, 1.35 mmol) was added to a solution of methyl 4-hydroxy-benzofuran-2-ylcarboxylate (240 mg, 1.25 mmol) in DMF (5 ml). After stirring for 10 min methyl iodide (888 mg, 6.25 mmol) was added and stirring was continued for an additional 1 h. The reaction was carefully quenched with water (30 ml) and diluted with ethyl acetate (50 ml). The separated organic layer was washed with 0.5M aqueous HCl, saturated aqueous sodium bicarbonate solution (50 ml), dried over sodium sulfate, and concentrated in vacuo to give pure methyl 4-methoxy-benzofuran-2-ylcarboxylate (257 mg, 1.25 mmol) as a white solid.

Workup

  1. additionwas added
  2. customThe reaction was carefully quenched with water (30 ml)
  3. additiondiluted with ethyl acetate (50 ml)
  4. washThe separated organic layer was washed with 0.5M aqueous HCl, saturated aqueous sodium bicarbonate solution (50 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d92cf773d0f4767b644e7934b4afd69
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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