Ethanol → Ethyl-4-(3-fluoro-2-methoxyphenyl)-2-oxo-4-methyl-valerate

HRID 1444396Notes

Reaction equation

HRID 1444396 reaction equation
[F:1][C:2]1[C:3]([O:17][CH3:18])=[C:4]([C:8]([CH3:16])([CH3:15])[CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH2:24](O)[CH3:25]>>[CH2:24]([O:12][C:11](=[O:13])[C:10](=[O:14])[CH2:9][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[O:17][CH3:18])([CH3:16])[CH3:15])[CH3:25]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 179890854-(3-Fluoro-2-methoxyphenyl)-4-methyl-2-oxo-pentanoic acid

Product 1

HCID 17989088Ethyl-4-(3-fluoro-2-methoxyphenyl)-2-oxo-4-methyl-valerateYield 90.6%

Procedure

4.14 g (16.28 mmol) of 4-(3-fluoro-2-methoxyphenyl)-4-methyl-2-oxo-pentanoic acid is dissolved in 97 ml of ethanol, mixed with 1.79 ml of sulfuric acid and refluxed for four hours. The ethanol is drawn off in a rotary evaporator, and the residue is carefully mixed with saturated sodium bicarbonate solution until a pH of 9 is reached. It is extracted twice with 100 ml each of ethyl acetate, and the combined organic extracts are washed with water and then with brine. After the desiccant is dried and filtered off, and after the solvent is spun in, the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 4.16 g (90.6%) of the desired compound is isolated.

Workup

  1. temperaturerefluxed for four hours
  2. customThe ethanol is drawn off in a rotary evaporator
  3. additionthe residue is carefully mixed with saturated sodium bicarbonate solution until a pH of 9
  4. extractionIt is extracted twice with 100 ml each of ethyl acetate
  5. washthe combined organic extracts are washed with water
  6. customAfter the desiccant is dried
  7. filtrationfiltered off
  8. customis chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ecbc22b2dfdd46b0bb04000736aeefcf
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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