Acetic Acid → HCID 19913834, compound

HRID 1090799Notes

Reaction equation

HRID 1090799 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].[CH3:9][O:10][C:11](=[O:16])[CH2:12][C:13]([CH3:15])=[O:14].C[C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[O:27])OC[O:23][C:22]=2[CH:28]=1.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[OH:23][C:22]1([CH3:1])[CH:28]=[CH:18][CH:19]=[CH:20][CH:21]1[C:26](=[O:27])[CH2:15][C:13](=[O:14])[CH2:12][C:11]([O:10][CH3:9])=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 2724682Lithium diisopropylamideHCID 19913828HCID 19913828, compound

Product 1

HCID 19913834HCID 19913834, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 41.6 mmol of lithium diisopropyl amide in tetrahydrofuran (formed by adding n-butyl lithium in hexanes to diisopropyl amine in THF) is added 2.4 g (20.8 mmole) of methylacetoacetate over 10 minutes at 0° C. After stirring for 30 minutes, 2.0 g of 7-methyl-1,3-benzodioxane-4-one is added and the mixture stirred for 30 minutes. 6 ml of acetic acid is added and the mixture diluted with ethyl acetate and filtered. The ethyl acetate solution is washed with diluted hydrochloric acid, water and dried over sodium sulfate. The ethyl acetate is removed in vacuo to give methyl 5-(2-hydroxy-2-methylphenyl)-3,5-dioxopentanoate.

Workup

  1. stirringthe mixture stirred for 30 minutes
  2. filtrationfiltered
  3. washThe ethyl acetate solution is washed with diluted hydrochloric acid, water
  4. dry with materialdried over sodium sulfate
  5. customThe ethyl acetate is removed in vacuo

Sources & evidence

ORD record
ord-68d0a3ec0aee4bb1a8c7f698c8cd0191
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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