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

HRID 981527ノート

反応式

HRID 981527 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-749284c3de2b4b20828230b59702ce76
出典データセット
uspto-grants-1991_02
特許番号
US04992447

反応ノート

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