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

HRID 359557Notes

Reaction equation

HRID 359557 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].ClC([O:19][CH2:20][CH3:21])=O.N1[CH:27]=[CH:26][CH:25]=CC=1.[CH2:28](Cl)Cl.C([O-])(O)=O.[Na+]>>[CH3:28][C:26]([CH3:25])([CH2:27][C:20](=[O:19])[CH3:21])[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 516892Sodium BicarbonateHCID 10242207HCID 10242207, compoundHCID 131716811HCID 131716811, 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 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. customdried
  4. custom(MgSO4) Removal of the volatiles in vacuo

Sources & evidence

ORD record
ord-957571a363c84ee4a8b1ab39a219f560
Source dataset
uspto-grants-1991_03
Patent number
US05001144

Reaction notes

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