Methyl 3-oxovalerate → HCID 57466732, compound

HRID 2219326Notes

Reaction equation

HRID 2219326 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].C[O-].[Na+].O/[N:14]=[C:15](\Cl)/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[CH3:1][O:2][C:3]([C:4]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:14][O:8][C:5]=1[CH2:6][CH3:7])=[O:9]

Participants

5

Reactant 3

HCID 121699Methyl 3-oxovalerateHCID 5706359Alpha-chlorobenzaldoximeHCID 10942334Sodium Methoxide

Product 1

HCID 57466732HCID 57466732, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of 3-oxo-pentanoic acid methyl ester (19.3 g, 0.15 mol) in methanol (30 mL) was added a solution of sodium methoxide (8.1 g, 0.15 mol) in methanol (30 mL) dropwise under ice-bath cooling keeping the temperature below 30° C. The reaction mixture was then stirred at room temperature for 30 min. Then a solution of (E)- and/or (Z)-N-hydroxy-benzenecarboximidoyl chloride (21.7 g, 0.14 mol, in Example 1a) in methanol (78 mL) was added to this mixture under ice-bath cooling keeping the temperature below 0° C. After adding, the ice-bath was removed and stirring was continued overnight at room temperature. The resulting mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The aqueous phase was further extracted with ethyl acetate. The combined organic extracts were then dried over sodium sulphate and concentrated to give the title compound as a yellow oil which was used in the next reaction without further purification. MS: m/e=232.1 [M+H]+.

Workup

  1. temperaturecooling
  2. customthe temperature below 30° C
  3. temperaturecooling
  4. customthe temperature below 0° C
  5. additionAfter adding
  6. customthe ice-bath was removed
  7. stirringstirring
  8. waitwas continued overnight at room temperature
  9. concentrationThe resulting mixture was concentrated under reduced pressure
  10. customthe residue was partitioned between ethyl acetate and water
  11. extractionThe aqueous phase was further extracted with ethyl acetate
  12. dry with materialThe combined organic extracts were then dried over sodium sulphate
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-f9e2f71f2cc54161bcd4c75ef4ad32d6
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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