Hydrochloric Acid → Ethyl 4-[2-(2-methylbenzimidazol-1-yl)ethoxy]-3-oxobutanoate

HRID 2292133ノート

反応式

HRID 2292133 の反応式
[H-].[Na+].[CH3:3][C:4]1[N:8]([CH:9](O)[CH3:10])[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[N:5]=1.Cl[CH2:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl.[O:27]1CCCC1>>[CH3:3][C:4]1[N:8]([CH2:9][CH2:10][O:27][CH2:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[N:5]=1

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 212769632-Methylbenzimidazol-1-ylethanol

生成物 1

HCID 20070378Ethyl 4-[2-(2-methylbenzimidazol-1-yl)ethoxy]-3-oxobutanoate収率 59%

実験手順

Sodium hydride (1.46 g, 80% suspension in oil) was suspended in dry tetrahydrofuran (60 ml) under nitrogen. 2-Methylbenzimidazol-1-ylethanol (4.3 g) was added and the suspension was sonicated at 40° C. for 2 hours. Ethyl 4-chloroacetoacetate (4.02 g) in tetrahydrofuran (20 ml) was added dropwise and sonication continued for a further 6 hours. The reaction was poured into 1N hydrochloric acid (50 ml), the tetrahydrofuran was removed under reduced pressure and the aqueous phase washed with toluene. The aqueous phase was adjusted to pH7 with potassium carbonate and extracted with dichloromethane (2×100 ml). The organic extracts were combined, dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was chromatographed on silica eluting with 5% methanol in ethyl acetate. The fractions containing the product were combined and evaporated to yield the title compound (4.4 g, 59%) as a red oil.

後処理

  1. customthe suspension was sonicated at 40° C. for 2 hours
  2. customsonication
  3. customthe tetrahydrofuran was removed under reduced pressure
  4. washthe aqueous phase washed with toluene
  5. extractionextracted with dichloromethane (2×100 ml)
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe residue was chromatographed on silica eluting with 5% methanol in ethyl acetate
  9. additionThe fractions containing the product
  10. customevaporated

出典と根拠

ORDレコード
ord-da3e5204aa874315a44e514dcd510bc6
出典データセット
uspto-grants-1989_01
特許番号
US04801598

反応ノート

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