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

HRID 1762961Notes

Reaction equation

HRID 1762961 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5f9f7963c1ce45ff8de7513d425e71ce
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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