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

HRID 981527노트

반응식

HRID 981527 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-749284c3de2b4b20828230b59702ce76
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04992447

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