Hydrochloric Acid → Ethyl 4-[2-(2-propylimidazol-1-yl)propoxy]-3-ketobutanoate

HRID 1721889Notes

Reaction equation

HRID 1721889 reaction equation
[CH2:1]([C:4]1[N:5]([CH:9]([CH3:12])[CH2:10][OH:11])[CH:6]=[CH:7][N:8]=1)[CH2:2][CH3:3].[CH2:13]([O:15][C:16](=[O:22])[CH2:17][C:18]([CH2:20]Cl)=[O:19])[CH3:14].Cl>O1CCCC1>[CH2:1]([C:4]1[N:5]([CH:9]([CH3:12])[CH2:10][O:11][CH2:20][C:18](=[O:19])[CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:22])[CH:6]=[CH:7][N:8]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69484Ethyl 4-chloroacetoacetateHCID 200703742-(2-Propylimidazol-1-yl)propan-1-ol

Product 1

HCID 20070369Ethyl 4-[2-(2-propylimidazol-1-yl)propoxy]-3-ketobutanoateYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-propylimidazol-1-yl)propan-1-ol (from Preparation 1 above) (5.4 g) was added and the suspension was sonicated until there was no further gas evolution. Ethyl-4-chloroacetoacetate (4.83 g) in tetrahydrofuran (10 ml) was added over 5 minutes with sonication and sonication continued at 25°-35° C. for a further 4 hours. The suspension was poured into 2N hydrochloric acid (30 ml) and the tetrahydrofuran removed under reduced pressure. The aqueous solution was washed with toluene (30 ml) and then neutralised with potassium carbonate. The aqueous solution was extracted with dichloromethane (3×100 ml), the combined organic extracts dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was chromatographed over silica eluting with a mixture of methanol and ethyl acetate (1:9) yielding the title compound as a pale red oil 3.5 g (40%).

Workup

  1. customthe suspension was sonicated until there
  2. customthe tetrahydrofuran removed under reduced pressure
  3. washThe aqueous solution was washed with toluene (30 ml)
  4. extractionThe aqueous solution was extracted with dichloromethane (3×100 ml)
  5. dry with materialthe combined organic extracts dried over magnesium sulphate
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was chromatographed over silica eluting with a mixture of methanol and ethyl acetate (1:9)

Sources & evidence

ORD record
ord-351c3325877147fe94f5db36cedc4a52
Source dataset
uspto-grants-1989_08
Patent number
US04853392

Reaction notes

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