Hydrochloric Acid → 4-Hydroxy-6-(4-methoxy-phenyl)-2-oxo-2H-chromene-3-carboxylic acid methyl ester

HRID 2190903Notes

Reaction equation

HRID 2190903 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](OB(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][C:11]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)=[CH:10][CH:9]=2)=[O:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 147699944-Methoxyphenyl boric acidHCID 866494596-bromo-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester

Product 1

HCID 866494584-Hydroxy-6-(4-methoxy-phenyl)-2-oxo-2H-chromene-3-carboxylic acid methyl esterYield 68.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 6-bromo-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (150 mg, 0.5 mmol; example 2-b) in dimethoxyethane (DME) was added 4-methoxyphenylboroic acid (92 mg, 0.6 mmol), tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) and 2N aq Na2CO3 (0.62 mL). The resulting mixture was purged with N2 for 1 min and heated to reflux for 2 h. Reaction mixture was diluted with water (50 mL) and acidified by 1 N aq HCl to pH=3-4. Precipitate was collected and dissolved in EtOAc. Insoluble was filtered off and the filtrate was dried over MgSO4, filtered, and concentrated. The crude product was triturated with MeOH (10 mL) and filtered. Resulting solid was dried in vacuo to give the title compound (112 mg). MS ESI(+) m/e: 327 (M+1).

Workup

  1. customThe resulting mixture was purged with N2 for 1 min
  2. temperatureheated
  3. temperatureto reflux for 2 h
  4. customReaction mixture
  5. customPrecipitate was collected
  6. dissolutiondissolved in EtOAc
  7. filtrationInsoluble was filtered off
  8. dry with materialthe filtrate was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was triturated with MeOH (10 mL)
  12. filtrationfiltered
  13. customResulting solid
  14. customwas dried in vacuo

Sources & evidence

ORD record
ord-e340b7bb8eef41139c0127027928d318
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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