Potassium Carbonate → HCID 54712963, compound

HRID 857521Notes

Reaction equation

HRID 857521 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.Br[CH:14]([CH2:20][CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:18]([O:17][C:15](=[O:16])[CH:14]([C:3]1[C:4](=[O:12])[O:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:20][CH3:21])[CH3:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 546829304-Hydroxycoumarin

Product 1

HCID 54712963HCID 54712963, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-chromen-2-one (2.0 g) and ethyl 2-bromobutyrate (2 mL) in DMF was added anhydrous potassium carbonate (8.5 g). The resulting reaction mixture was stirred at room temperature for 72 hours, then diluted with water and extracted with EtOAc. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over MgSO4 and conc. in vacuo to provide colorless oil, which was purified by column chromatography to give 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl) -butyric acid ethyl ester as a white solid, MS: 275[M−H].

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over MgSO4 and conc. in vacuo
  5. customto provide colorless oil, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-99ac28dd4efc4d838a608cd620f9aff7
Source dataset
uspto-grants-2006_12
Patent number
US07145020B2

Reaction notes

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