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

HRID 844429Notes

Reaction equation

HRID 844429 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].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:25](O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>C1COCC1>[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][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:11]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 72899Indole-2-carboxylic acid

Product 1

HCID 7723355benzyl 1H-indole-2-carboxylateYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.32 g of 2-indolecarboxylic acid in 70 ml of THF are placed in a three-necked flask at RT, 10.38 g of carbonyldiimidazole are added and, after the evolution of gas has ceased, 7.62 g of benzyl alcohol are then added. After refluxing for 5 hours, the mixture is poured into water and extracted with DCM, and the extracts are dried and evaporated. The crystals formed are washed with iPrOH to give 13.62 g of the expected compound: m.p.=136° C.

Workup

  1. temperatureAfter refluxing for 5 hours
  2. extractionextracted with DCM
  3. customthe extracts are dried
  4. customevaporated
  5. customThe crystals formed
  6. washare washed with iPrOH

Sources & evidence

ORD record
ord-1abefade2e524a32b0f474e866a99830
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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