Benzyl Alcohol → benzyl 1H-indole-2-carboxylate

HRID 2082404Notes

Reaction equation

HRID 2082404 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].[CH2:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 72899Indole-2-carboxylic acid

Product 1

HCID 7723355benzyl 1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g of N,N'-carbonyldiimidazole are introduced into a solution of 5 g of indole-2-carboxylic acid in 50 ml of dry tetrahydrofuran; after stirring for 12 hours at ambient temperature, 3.7 g of benzyl alcohol are added and the reaction mixture is brought to its reflux temperature; this is maintained for 8 hours, before removing the solvent by distillation under reduced pressure. The residue is dissolved in ethyl acetate and the organic phase is washed with a N aqueous NaOH solution and then dried before evaporation of the solvent.

Workup

  1. temperaturereflux temperature
  2. temperaturethis is maintained for 8 hours
  3. custombefore removing the solvent
  4. distillationby distillation under reduced pressure
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washthe organic phase is washed with a N aqueous NaOH solution
  7. customdried before evaporation of the solvent

Sources & evidence

ORD record
ord-a00633d2737c4d50857a2c1542c6fc94
Source dataset
uspto-grants-1993_02
Patent number
US05189049

Reaction notes

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