Hydrochloric Acid → Ethyl 5-(3-chlorophenyl)-3-oxopentanoate

HRID 324441Notes

Reaction equation

HRID 324441 reaction equation
[Li+].CC([N-]C(C)C)C.[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br.Cl>O1CCCC1>[Cl:18][C:19]1[CH:20]=[C:21]([CH2:22][CH2:13][C:11](=[O:12])[CH2:10][C:9]([O:15][CH2:16][CH3:17])=[O:14])[CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 2724682Lithium diisopropylamide

Product 1

HCID 20462750Ethyl 5-(3-chlorophenyl)-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of LDA (2.0M solution in heptanes/tetrahydrofuran/ethylbenzene, 500 ml) in tetrahydrofuran (2 L) at 0° C. was added ethyl acetoacetate (62 ml). After 40 min 3-chlorobenzyl bromide (100 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 ethyl acetate and washed with water and brine, dried (MgSO4) and evaporated. 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 ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification
  7. washeluting with 5-10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-597121b0d5e947ce86f54bee3d04c4c6
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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