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Dimethylformamide → 3-Methyl-4-(pyridin-3-ylmethoxy)-benzofuran-2-carboxylic acid t-butyl ester

HRID 29484
Notes
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Reaction equation

HRID 29484 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].[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25]Cl)[CH:20]=1.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][CH2:25][C:21]3[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=3)[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 183583-(Chloromethyl)pyridineHCID 138494564-Hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687169743-Methyl-4-(pyridin-3-ylmethoxy)-benzofuran-2-carboxylic acid t-butyl esterYield 90%

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 mmol), 3-picolyl chloride (1.1 equiv.) potassium carbonate (5 equiv.) and 10 mL 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 afforded 3-methyl-4-(pyridin-3-ylmethoxy)-benzofuran-2-carboxylic acid t-butyl ester as a thick oil in 90% 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-283ee1398f014fee8050dfa0cf6b04c0
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