Hydrochloric Acid → Methyl 3-oxo-6-heptenoate

HRID 465538Notes

Reaction equation

HRID 465538 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:11]([Li])[CH2:12][CH2:13]C.C(Br)C=C.Cl>O1CCCC1.CCCCCC.CCOCC.O>[O:4]=[C:3]([CH2:5][CH2:13][CH:12]=[CH2:11])[CH2:2][C:1]([O:7][CH3:8])=[O:6]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 366065Methyl 3-oxo-6-heptenoate

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Methyl acetoacetate (34.8 g) is added dropwise to a suspension of 16.2 g of 50% sodium hydride in mineral oil in 750 ml of anhydrous tetrahydrofuran cooled to 0°. To this solution is added dropwise 141 ml of a 2.3M solution of n-butyllithium in hexane over 40 min keeping the temperature of the THF solution at 0°. To this solution is then added 36 g of a solution of allyl bromide in 150 ml of THF. After 10 min the reaction is worked up by pouring into a mixture of 60 ml of aqueous concentrated HCl, 150 ml of water and 500 ml of ether. The ether layer is separated, washed with water, dried over magnesium sulfate, filtered and evaporated to give methyl 3-oxo-hept-6-enoate.

Workup

  1. temperaturecooled to 0°
  2. customat 0°
  3. customThe ether layer is separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e1eeafa20c684d33bfb99ee54daca98f
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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