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

HRID 1762961노트

반응식

HRID 1762961 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5f9f7963c1ce45ff8de7513d425e71ce
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04835175

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