Ethyl Acetoacetate → Ethyl 3-oxo-5-m-toluylpentanoate

HRID 324420Notes

Reaction equation

HRID 324420 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C([N-]C(C)C)(C)C.[Li+].[CH3:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br>O1CCCC1>[CH3:18][C:19]1[CH:20]=[C:21]([CH2:22][CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 12099m-Xylyl bromideHCID 2724682Lithium diisopropylamide

Product 1

HCID 54309110Ethyl 3-oxo-5-m-toluylpentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl acetoacetate (74.5 ml) was added dropwise to a solution of lithium diisopropylamide (2.0M solution in heptane/tetrahydrofuran/ethylbenzene, 600 ml) in tetrahydrofuran (2.5 L) at 0° C. The mixture was stirred for 30 min then 3-methylbenzylbromide (79 ml) was added dropwise. The mixture was stirred for 1 hour at 0° C. then quenched with 2M HCl. The mixture was extracted with ethyl acetate, the extracts washed with water, dried (MgSO4) and evaporated to give an oil which was purified by chromatography eluting with 5-10% ethyl acetate in isohexane.

Workup

  1. stirringThe mixture was stirred for 1 hour at 0° C.
  2. customthen quenched with 2M HCl
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extracts washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give an oil which
  8. customwas purified by chromatography
  9. washeluting with 5-10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-4567031854d64034950188e2e4720135
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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