Citric Acid → (1,2-Dimethyl-1H-benzo[d]imidazol-5-yl)methanol

HRID 928447ノート

反応式

HRID 928447 の反応式
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](OC)=[O:12])=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:15].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.CC(=O)OCC>C1COCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:15]

参加物

6

反応物 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 62649Sodium sulfate decahydrateHCID 21998749Methyl 1,2-dimethyl-1H-benzo[d]imidazole-5-carboxylate

生成物 1

HCID 2998315(1,2-Dimethyl-1H-benzo[d]imidazol-5-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of Methyl 1,2-dimethyl-1H-benzo[d]imidazole-5-carboxylate (500 mg, 2.448 mmol) in THF (24.5 ml) Lithiumaluminium hydride (1 M in THF, 2.44 ml) was added at 0° C. After 2 hours sodium sulfate decahydrate and citric acid was added to the reaction to destroy the excess of lithiumaluminiumhydride. After 1 hour, methanol (25 ml) was added and the fine suspension was filtered off. The filtrate was evaporated under reduced pressure to afford a brown solid. EA (50 ml) was added and the suspension was treated in an ultra sonic bath. The solid was filtered off and this procedure was repeated twice. The yellow filtrate was evaporated under reduced pressure to afford crude (1,2-Dimethyl-1H-benzo[d]imidazol-5-yl)methanol.

後処理

  1. customto destroy the excess of lithiumaluminiumhydride
  2. additionmethanol (25 ml) was added
  3. filtrationthe fine suspension was filtered off
  4. customThe filtrate was evaporated under reduced pressure
  5. customto afford a brown solid
  6. additionthe suspension was treated in an ultra sonic bath
  7. filtrationThe solid was filtered off
  8. customThe yellow filtrate was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-7018b9a92df343af9db66a8f7dd2e912
出典データセット
uspto-grants-2016_03
特許番号
US09290485B2

反応ノート

読み込み中…