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Methyl iodide → 4-Methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29406
Notes
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Reaction equation

HRID 29406 reaction equation
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].IC.[C:21]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:21])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 138494564-Hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687092194-Methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl esterYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester (300 mg, 1.21 mmol) was added iodomethane (0.75 mL, 10 eq), K2CO3 (332 mg, 2.4 mmol) and 2 mL of DMF. The mixture was stirred at room temperature overnight. The mixture was washed with brine and extracted with ethyl acetate. The combined ethyl acetate solution was washed with brine. Removal of the solvent gave 312 mg (98% yield) of 4-methoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester as an amber colored oil.

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate solution was washed with brine
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-d5ce94e7c6994ea488b001a89ad62487
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07420001B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes