Hydrochloric Acid → Methyl 3-oxohexanoate

HRID 1790884Notes

Reaction equation

HRID 1790884 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:10])[CH2:6][C:7]([CH3:9])=[O:8].[CH2:11]([Li])[CH2:12]CC.ICC.Cl>C(OCC)(=O)C.C1COCC1>[CH3:3][O:4][C:5](=[O:10])[CH2:6][C:7](=[O:8])[CH2:9][CH2:11][CH3:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 121700Methyl 3-oxohexanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

44.4 g of sodium hydride suspension (60% in paraffin oil) is introduced into 1500 ml of THF, and 107.5 ml of acetoacetic acid methyl ester 3 is added under nitrogen at 0° C. After 10 minutes, 440 ml of n-butyllithium solution (2.5 M in hexane) is then added in drops, and it is stirred for another 30 minutes at 0C. Now, 88.9 ml of iodoethane is added, and it is stirred overnight at room temperature. For working-up, it is again cooled to 0° C. and neutralized with 4N hydrochloric acid. The organic phase is diluted with ethyl acetate, washed with thiosulfate solution and sodium chloride solution, dried on sodium sulfate and concentrated by evaporation. The residue is then chromatographed on silica gel with ethyl acetate/hexane, whereby 95.13 g of title compound 13 is obtained as a colorless oil.

Workup

  1. additionis added under nitrogen at 0° C
  2. washwashed with thiosulfate solution and sodium chloride solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is then chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-dbe3e6451b744424b549660e3fb4baea
Source dataset
uspto-grants-2006_07
Patent number
US07071344B1

Reaction notes

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