Ethyl 4-hydroxy-6-methyl-2-heptynoate → Ethyl 6-methyl-4-oxo-2-heptynoate

HRID 1835157Notes

Reaction equation

HRID 1835157 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH:15]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:16]#[C:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CC(C)=O.O>[CH3:26][CH:24]([CH3:25])[CH2:23][C:15](=[O:14])[C:16]#[C:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 2

HCID 23503233Ethyl 4-hydroxy-6-methyl-2-heptynoateHCID 131709961Jones' reagent

Product 1

HCID 23503271Ethyl 6-methyl-4-oxo-2-heptynoateYield 74.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Jones' reagent (from chromium trioxide, 4 g) was added dropwise with stirring to ethyl 4-hydroxy-6-methyl-2-heptynoate (9.5 g) in acetone (30 ml) in an ice bath, with the temperature being maintained at about 10°. After 0.5 hour the reaction was diluted with water (300 ml) and extracted with diethyl ether thrice. The organic phase was washed with brine, dried, and evaporated to give ethyl 6-methyl-4-oxo-2-heptynoate as an oil (7.0 g).

Workup

  1. temperaturebeing maintained at about 10°
  2. extractionextracted with diethyl ether thrice
  3. washThe organic phase was washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-18f30e12de2e4b6ca9b51f66c7806f38
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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