Water → HCID 19373259, compound

HRID 1197367Notes

Reaction equation

HRID 1197367 reaction equation
[CH3:1][CH:2]([CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[CH2:18](I)[CH3:19].O>CN(C)C=O>[CH3:1][CH:2]([CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[CH2:3][C:4]([O:6][CH2:18][CH3:19])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 22743509HCID 22743509, compound

Product 1

HCID 19373259HCID 19373259, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-6-oxoheptanoic acid (2.45 g) was stirred in dry dimethylformamide (60 ml) at 20° C. and anhydrous sodium carbonate (1.64 g) was added. Ethyl iodide (5.4 ml) was added dropwise and the mixture was refluxed with stirring for 2 hours. The mixture was cooled, poured into water and the aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with saturated aqueous sodium thiosulphate solution, water, and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue was purified by chromatography on silica, eluting with 1:4 diethyl ether:hexane. Ethyl 3-methyl-6-oxoheptanoate was obtained as an orange oil (2.0 g)

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureThe mixture was cooled
  3. extractionthe aqueous mixture was extracted with diethyl ether
  4. washThe ethereal extracts were washed with saturated aqueous sodium thiosulphate solution, water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on silica
  8. washeluting with 1:4 diethyl ether

Sources & evidence

ORD record
ord-7c783f7d26e6403ebdf935e0061ecc9d
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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