Methyl 2-chloro-3-oxopentanoate → HCID 178437742, compound

HRID 1110945Notes

Reaction equation

HRID 1110945 reaction equation
C[O:2][C:3](=O)[CH:4]([Cl:9])[C:5](=O)[CH2:6][CH3:7].[Cl-].[CH:12]([NH2:14])=[NH2+:13].C[O-].[Na+]>CO>[Cl:9][C:4]1[C:3]([OH:2])=[N:13][CH:12]=[N:14][C:5]=1[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 545096Methyl 2-chloro-3-oxopentanoateHCID 10942334Sodium MethoxideHCID 11829351Formamidiniumchloride

Product 1

HCID 178437742HCID 178437742, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8.6 g (0.049 mol) of 2-chloro-3-oxopentanoic acid methylester (content 94 percent) and 6.04 g (0.075 mol) of formamidinium chloride in 10 ml of methanol, there was added within 2 hours at 20° to 22° C., while stirring, 21.6 g of sodium methylate solution (30 percent in methanol, 0.12 mol). After another 3 hours of stirring, neutralization with conc. hydrochloric acid (pH about 5) and evaporation to dryness on the rotary evaporator were performed. The residue was taken up with 20 ml of water and extracted out three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, the solvent was distilled off and the solid residue was dried at 50° C. and 100 torr. The following data concerns the product of this example:

Workup

  1. stirringAfter another 3 hours of stirring
  2. customneutralization with conc. hydrochloric acid (pH about 5) and evaporation to dryness
  3. customon the rotary evaporator
  4. extractionextracted out three times with ethyl acetate
  5. customThe combined organic phases were dried on sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe solid residue was dried at 50° C.

Sources & evidence

ORD record
ord-4923b823bc764cc5a7f1add7fba6bdf8
Source dataset
uspto-grants-1990_12
Patent number
US04977264

Reaction notes

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