Ethyl Acetate → HCID 22340444, compound

HRID 585312Notes

Reaction equation

HRID 585312 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12]([C:17](OCC)=[O:18])=[CH:11]3)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1>[Br:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12]([CH2:17][OH:18])=[CH:11]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22340427HCID 22340427, compound

Product 1

HCID 22340444HCID 22340444, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ethyl 5-[(4-bromobenzyl)oxy]-1H-indole-2-carboxylate (300 mg, 0.802 mmol) obtained in the above 1) in tetrahydrofuran (4 ml) was added lithium aluminum hydride (60.8 mg, 1.60 mmol) at 0° C., and the mixture was stirred for 1 hour. Ethyl acetate was added to the reaction solution, the mixture was washed with 1N hydrochloric acid and an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After the solvent was concentrated under reduced pressure, the resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate), and converted into powders with isopropyl ether and hexane to obtain the titled compound (219 mg).

Workup

  1. washthe mixture was washed with 1N hydrochloric acid
  2. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  3. concentrationAfter the solvent was concentrated under reduced pressure
  4. customthe resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-38ba1a52d9dd493884860dcdd20f0061
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

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