Dimethylformamide → 3,5-Dioxohexanoic acid

HRID 356586Notes

Reaction equation

HRID 356586 reaction equation
[I-].COC(=O)C(C)C1[C:15]2[C:10](=[CH:11][C:12]([OH:16])=[CH:13]C=2)C=CC=1.[C:19](=[O:22])([O-])[O-:20].[K+].[K+].CN(C)C=[O:28]>>[CH3:15][C:10]([CH2:11][C:12]([CH2:13][C:19]([OH:20])=[O:22])=[O:16])=[O:28]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 53803583HCID 53803583, compound

Product 1

HCID 54598443,5-Dioxohexanoic acidYield 64%

Procedure

The iodide 2 (286.6 mg) and 6-hydroxy-α-methylnaphthaleneacetic acid methyl ester (154.0 mg) were dissolved in dimethylformamide (3 ml) and potassium carbonate (277,6 mg) was added. The reaction was stirred at room temperature for 12 hours, after which it was partitioned between water (10 ml) 15 and ethyl acetate (50 ml). The layers were separated and the organics were washed with water (3×10 ml) and brine (10 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated to dryness. Purification of the residue on silica gel (25% ethyl acetate/hexane) gave the desired triacetate (225.8 mg, 64% yield).

Workup

  1. customafter which it was partitioned between water (10 ml) 15 and ethyl acetate (50 ml)
  2. customThe layers were separated
  3. washthe organics were washed with water (3×10 ml) and brine (10 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customPurification of the residue on silica gel (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-57372b18501d4bab88bece0e3350e155
Source dataset
uspto-grants-1998_11
Patent number
US05837689

Reaction notes

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