Phenacyl bromide → HCID 53869049, compound

HRID 1957802Notes

Reaction equation

HRID 1957802 reaction equation
[F-].[K+].[CH2:3](Br)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[OH:13][C:14]1[C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:27]([O:29][CH3:30])=[O:28])[CH:20]=2)[CH:15]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)C.C(OCC)(=O)C>[OH:13][C:14]1[C:23]([C:24]([O:26][CH2:3][C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[O:25])=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:27]([O:29][CH3:30])=[O:28])[CH:20]=2)[CH:15]=1

Participants

8

Reactant 4

HCID 6259Phenacyl bromideHCID 516892Sodium BicarbonateHCID 522689Potassium FluorideHCID 11746915HCID 11746915, compound

Product 1

HCID 53869049HCID 53869049, compoundYield 48.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To anhydrous N,N-dimethylformamide (hereinafter referred to as "DMF") (10.0 g) were added potassium fluoride (0.209 g) and phenacyl bromide (0.647 g), followed by stirring on an oil bath at 25° C. for about 1 minute. 2-Hydroxy-3-hydroxycarbonyl-6-methoxycarbonylnaphthalene (0.80 g) was dissolved in anhydrous DMF (5.20 g) and the resulting solution was added to the reaction solution. After the completion of the reaction, ethyl acetate, diethyl ether and aqueous 5% sodium hydrogencarbonate were added. Then, an insoluble matter was removed by filtration and the residue was partitioned. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure. The resultant residue was purified by subjecting to silica gel chromatography to obtain 0.57 g of 2-hydroxy-3-phenacyloxycarbonyl-6-methoxycarbonylnaphthalene (DSC analysis value: 177.7° C.).

Workup

  1. additionthe resulting solution was added to the reaction solution
  2. additionwere added
  3. customThen, an insoluble matter was removed by filtration
  4. customthe residue was partitioned
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter the desiccant was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resultant residue was purified

Sources & evidence

ORD record
ord-1a9148f5495943029e785d5d1958d368
Source dataset
uspto-grants-1998_07
Patent number
US05786523

Reaction notes

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