Benzyl Bromide → Ethyl 3-oxo-5-phenylpentanoate

HRID 490697

Reaction equation

HRID 490697 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.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH2:8]([O:7][C:1](=[O:6])[CH2:2][C:3](=[O:4])[CH2:5][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:9]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8868Ethyl AcetoacetateHCID 2724682Lithium diisopropylamide

Product 1

HCID 61162Ethyl 3-oxo-5-phenylpentanoateYield 36.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl acetoacetate (2.32 g, 20 mmol) is added to a pre-cold solution of LDA (2.0 M, 20 mL, 40 mmol) in THF (100 mL) at 0° C. After addition, the mixture is stirred for 30 min, then benzyl bromide (3.42 g, 20 mmol) is added dropwise. After stirred at 0° C. for 30 min, the reaction is quenched by 5 N HCl, extracted with ethyl ether. The combined organic layers are washed with water and brine until it is neutral. Concentration and column chromatography yields 1.6 g of the title compounds.

Workup

  1. additionAfter addition
  2. stirringAfter stirred at 0° C. for 30 min
  3. customthe reaction is quenched by 5 N HCl
  4. extractionextracted with ethyl ether
  5. washThe combined organic layers are washed with water and brine until it
  6. concentrationConcentration and column chromatography

Sources & evidence

ORD record
ord-ca2e0b6abdee40a588b3fecc526bdd5c
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Linked notes

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