Hydrochloric Acid → 5-(3-Ethylphenyl)-3-oxopentanoic acid, ethyl ester

HRID 324457Notes

Reaction equation

HRID 324457 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Li+].CC([N-]C(C)C)C.Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][CH3:27])[CH:21]=1.Cl>O1CCCC1>[CH2:26]([C:22]1[CH:21]=[C:20]([CH2:19][CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH:25]=[CH:24][CH:23]=1)[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 2724682Lithium diisopropylamideHCID 220036561-(Bromomethyl)-3-ethylbenzene

Product 1

HCID 1317225225-(3-Ethylphenyl)-3-oxopentanoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of ethyl acetoacetate (25 g) in tetrahydrofuran (800 ml) at 0° C. was added LDA (2.0M solution in heptanes/tetrahydrofuran/ethylbenzene) (194 ml). After 40 min the product from step (ii) (39 g) was added dropwise and the mixture was stirred at 0° C. for 1 hour. The reaction mixture was acidified with 2N HCl and the organic phase was concentrated under reduced pressure. The residue was dissolved in diethyl ether and washed with water and saturated brine. The organic phase was collected, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 5-10% ethyl acetate in isohexane.

Workup

  1. concentrationthe organic phase was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in diethyl ether
  3. washwashed with water and saturated brine
  4. customThe organic phase was collected
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customPurification
  8. washeluting with 5-10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-73ed8243998840b595c74f846fe74f5d
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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