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Ethyl bromoacetate → 6-tert-Butyl 2-ethyl 1-benzofuran-2,6-dicarboxylate

HRID 2371066
Notes
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Reaction equation

HRID 2371066 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][C:4]=1[OH:16])=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C>[O:16]1[C:4]2[CH:5]=[C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:14]=[CH:15][C:3]=2[CH:1]=[C:24]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 11430Potassium CarbonateHCID 58247952Tert-butyl 4-formyl-3-hydroxybenzoate

Product 1

HCID 582479886-tert-Butyl 2-ethyl 1-benzofuran-2,6-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of tert-butyl 4-formyl-3-hydroxybenzoate (1.2 g, 5.40 mmol) and potassium carbonate (1726 mg, 12.4 mmol) in DMF (17 ml) was admixed dropwise with ethyl bromoacetate (0.56 ml, 5.0 mmol) and stirred at 80° C., for 6 h. Then ethyl bromoacetate (0.28 ml, 2.5 mmol) was added again and the mixture was stirred at 80° C. overnight. After cooling to room temperature, the reaction mixture was added to ice-water and extracted with ethyl acetate. The organic phases were dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure.

Workup

  1. stirringthe mixture was stirred at 80° C. overnight
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c422d02c4c5f4b598027e679a1b8d995
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08710242B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes