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

HRID 2165132Notes

Reaction equation

HRID 2165132 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]>>[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

3

Reactant 2

HCID 8858Mesityl oxideHCID 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) (26.95 g, 0.128 mol) and mesityl oxide (2) (19.3 g, 0.192 mol) was kept at 0°-5° C. for 5 days, poured onto cold saturated NaHC3 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-30f618c810884cd19c238bb8a1e27f2a
Source dataset
uspto-grants-1990_07
Patent number
US04939143

Reaction notes

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