Ethyl Acetate → HCID 22676901, compound

HRID 1006314Notes

Reaction equation

HRID 1006314 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]2[CH:5]([C:6](=[O:16])[C:7]([C:13]([OH:15])=[O:14])=[CH:8][O:9]2)[CH:4]=1)[CH3:2].[CH2:17]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[O:25][CH:24]=[C:23](C=O)[C:22]2=[O:31])[CH3:18].[OH:32]OS([O-])=O.[K+].CCOC(C)=O>CN(C=O)C>[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]2[CH:5]([C:6](=[O:16])[C:7]([C:13]([OH:15])=[O:14])=[CH:8][O:9]2)[CH:4]=1)[CH3:2].[CH2:17]([C:19]1[CH:28]=[CH:27][CH:26]2[CH:21]([C:22](=[O:31])[C:23]([OH:32])=[CH:24][O:25]2)[CH:20]=1)[CH3:18]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 27588496-Ethyl-3-formylchromoneHCID 22676903HCID 22676903, compoundHCID 23707502Potassium hydroxy sulfite

Product 2

HCID 22676901HCID 22676901, compoundHCID 22676903HCID 22676903, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To prepare 6-ethyl-4-oxo-4a,8a-dihydro-4H-chromene-3-carboxylic acid, 6-ethyl-3-formyl chromone (0.25 g) was dissolved in DMF (10 mL), and OXONE (0.76 g) was added and stirred at room temperature for 3 hours with the reaction having a final volume (12 mL). The reaction was monitored by TLC or GC analysis. EtOAc was added to extract the products and 1N HCl was used to dissolve the salts. The organic extract was washed with 1N HCl (30 mL×3) and brine (30 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 6-ethyl-4-oxo-4a,8a-dihydro-4H-chromene-3-carboxylic acid in 52% yield and 6-ethyl-3-hydroxy-4a,8a-dihydro-chromene-4-one in 34% yield after purification by silica gel column chromatography.

Workup

  1. extractionto extract the products and 1N HCl
  2. dissolutionto dissolve the salts
  3. extractionThe organic extract
  4. washwas washed with 1N HCl (30 mL×3) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c16e355a8281464fab3f8c305bce874c
Source dataset
uspto-grants-2004_09
Patent number
US06787671B2

Reaction notes

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