Dimethylformamide → HCID 68716632, compound

HRID 29482Notes

Reaction equation

HRID 29482 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][CH3:24])=[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][CH3:24])=[O:22])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 60984Methyl bromoacetateHCID 138494564-Hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 68716632HCID 68716632, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round-bottom flask with stir bar was added 4-hydroxy-3-methyl-benzofuran-2 carboxylic acid t-butyl ester (1 mmole), methyl 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 solvent gave 4-methoxycarbonylmethoxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester as a thick oil in 92% yield.

Workup

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

Sources & evidence

ORD record
ord-6e42a6834ffc44ac8b9028298d0a2c85
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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