Methyl iodide → 4-Methoxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29429Notes

Reaction equation

HRID 29429 reaction equation
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[C:14]([OH:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].IC.[C:23]([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][C:15]([CH2:18][OH:19])=[C:14]([O:20][CH3:23])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 687148834-Hydroxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687152574-Methoxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl esterYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 190 mg of 4-hydroxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was added 1 mL of iodomethane, 200 mg of K2CO3 and 3 mL of DMF. The mixture was stirred at room temperature overnight. The reaction mixture was washed with brine and extracted with ethyl acetate. The combined ethyl acetate solution was washed with brine. Removal of the solvent gave 200 mg of 4-methoxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester as a pale yellow oil.

Workup

  1. washThe reaction 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-5707b73b656e4248b54cae0d228be7a4
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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