Dimethylformamide → 4-Ethoxycarbonylmethoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29480Notes

Reaction equation

HRID 29480 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].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].CN(C=O)C>O>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 138494564-Hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687149594-Ethoxycarbonylmethoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottom flask with a stir bar was added 4-hydroxy-3-methyl-benzofuran-2 carboxylic acid t-butyl ester (1 mmol), ethyl 2-bromoacetate (1.1 eq.) potassium carbonate (5 equiv.), and 10 mL of DMF. The reaction mixture was stirred overnight and then slowly added dropwise to water (10 mL) with stirring. The resulting mixture was extracted with ethyl acetate (2×20 mL), brine (20 mL), dried over magenesium sulfate. Filtration and evaporation of the solvent gave 4-ethoxycarbonylmethoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester as a thick oil in 90% yield.

Workup

  1. stirringwith stirring
  2. extractionThe resulting mixture was extracted with ethyl acetate (2×20 mL), brine (20 mL)
  3. dry with materialdried over magenesium sulfate
  4. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-950dceff36ee4758b28dfce462a94429
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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