Methyl 4-hydroxyhex-2-ynoate → HCID 13237261, compound

HRID 734361Notes

Reaction equation

HRID 734361 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C:4]#[C:5][CH:6]([OH:9])[CH2:7][CH3:8].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:1][O:2][C:3](=[O:10])[C:4]#[C:5][C:6](=[O:9])[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 13859766Methyl 4-hydroxyhex-2-ynoateHCID 131709961Jones' reagent

Product 1

HCID 13237261HCID 13237261, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl-4-hydroxy-2-hexynoate (25.0 g, 176 mmol) in acetone (200 mL), cooled in an ice water bath, was added Jones reagent (70 mL of 3.2 M chromium VI oxide in 1:3 sulfuric acid:water). The reaction mixture was allowed to stir at room temperature for 3 h then filtered through a plug of diatomaceous earth and the filter cake was rinsed with dichloromethane (2×100 mL). The organic phase was saved and the aqueous phase was extracted with dichloromethane (2×100 mL). The combined organic phases were washed with saturated sodium bicarbonate (2×200 mL), dried (sodium sulfate) and concentrated to provide 17.0 g (69%) of 4-oxo-hex-2-ynoic acid methyl ester.

Workup

  1. filtrationthen filtered through a plug of diatomaceous earth
  2. washthe filter cake was rinsed with dichloromethane (2×100 mL)
  3. extractionthe aqueous phase was extracted with dichloromethane (2×100 mL)
  4. washThe combined organic phases were washed with saturated sodium bicarbonate (2×200 mL)
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f87487f04ed1430b91d3dfb8824db8da
Source dataset
uspto-grants-2009_09
Patent number
US07592353B2

Reaction notes

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