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

HRID 29489Notes

Reaction equation

HRID 29489 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]([N:23]([CH3:25])[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:22])[N:23]([CH3:25])[CH3:24])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2255442-Bromo-N,N-dimethylacetamideHCID 138494564-Hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687161964-Dimethylcarbamoylmethoxy-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), α-bromo-N,N-dimethylacetamide (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), washed with brine (20 ml), dried over MgSO4. Filtration and evaporation of the solvent gave 4-dimethylcarbamoylmethoxy-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)
  3. washwashed with brine (20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-913dd664560b443d8b21c28c7188c876
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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