Benzyl Bromide → Ethyl 7-(benzyloxy)-4-formyl-1H-indole-2-carboxylate

HRID 1762961ノート

反応式

HRID 1762961 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH:15]=[O:16])[CH:11]=[CH:10][C:9]=2[OH:17])=[O:5])[CH3:2].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([CH:15]=[O:16])[CH:11]=[CH:10][C:9]=2[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13243483Ethyl 4-formyl-7-hydroxy-1H-indole-2-carboxylate

生成物 1

HCID 13243484Ethyl 7-(benzyloxy)-4-formyl-1H-indole-2-carboxylate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

2.33 g of 4-formyl-7-hydroxyindole-2-carboxylic acid ethyl ester is combined with 1.8 ml of benzyl bromide, 1 g of potassium carbonate, and 100 ml of acetone and heated under reflux for 4 hours. The reaction mixture is then evaporated to dryness, combined with water, and extracted with ethyl acetate. The organic phase is washed twice with saturated sodium bicarbonate solution, dried over sodium sulfate, concentrated, and recrystallized from ethyl acetate/hexane, thus obtaining 1.8 g of 7-benzyloxy-4-formylindole-2-carboxylic acid ethyl ester, mp 131°-132° C.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customThe reaction mixture is then evaporated to dryness
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed twice with saturated sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customrecrystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-5f9f7963c1ce45ff8de7513d425e71ce
出典データセット
uspto-grants-1989_05
特許番号
US04835175

反応ノート

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