Mesityl oxide → Methyl α-(1,1-dimethyl-3-oxobutyl)-4-fluoro-3-methyl-β-oxobenzenepropanoate

HRID 654538Notes

Reaction equation

HRID 654538 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:7])=[CH:4][C:3]=1[CH3:15].[O:16]=[C:17]([CH:19]=[C:20]([CH3:22])[CH3:21])[CH3:18].C([O-])(O)=O.[Na+]>>[CH3:21][C:20]([CH3:22])([CH2:19][C:17](=[O:16])[CH3:18])[CH:8]([C:6](=[O:7])[C:5]1[CH:13]=[CH:14][C:2]([F:1])=[C:3]([CH3:15])[CH:4]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 3

HCID 8858Mesityl oxideHCID 516892Sodium BicarbonateHCID 10242207HCID 10242207, compound

Product 1

HCID 15056950Methyl α-(1,1-dimethyl-3-oxobutyl)-4-fluoro-3-methyl-β-oxobenzenepropanoate

Procedure

A mixture of methyl 4-fluoro-3-methylbenzoylacetate (1a) (26.95g, 0.128 mol) and mesityl oxide (2) (19.3g, 0.192 mol) was kept at 0°-5° C. for 5 days, poured onto cold saturated NaHCO3 and extracted with ether. The combined extracts were washed with H2O and brine and dried (MgSO4). Removal of the volatiles in vacuo furnished 3a which was used without further purification.

Workup

  1. extractionextracted with ether
  2. washThe combined extracts were washed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. customRemoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-68b7a1cddf724675810eae7d015fe7df
Source dataset
uspto-grants-1992_07
Patent number
US05132312

Reaction notes

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