Stearic Acid → 1H-Indole-2-carboxylic acid, 3-(1-oxododecyl)-, ethyl ester

HRID 382827Notes

Reaction equation

HRID 382827 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]([O:12][CH2:13][CH3:14])=[O:11].[C:15](O)(=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]CCCCCC.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[C:15]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 5281Stearic AcidHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 106192401H-Indole-2-carboxylic acid, 3-(1-oxododecyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.8 g (20 mmol) of ethyl indole-2-carboxylate, 6.0 g (30 mmol) of octadecanoic acid, 1.0 g of polyphosphoric acid, 20 ml of absol. CH2Cl2 and 4.4 ml of trifluoroacetic anhydride is stirred at room temperature for 4 h. Then 1 M NaOH is added, and the mixture is extracted with ether. The ether phase is dried over Na2SO4 and the solvent is distilled off. The product precipitates after addition of petroleum ether.

Workup

  1. extractionthe mixture is extracted with ether
  2. dry with materialThe ether phase is dried over Na2SO4
  3. distillationthe solvent is distilled off
  4. customThe product precipitates
  5. additionafter addition of petroleum ether

Sources & evidence

ORD record
ord-0563c47bc0a54358ac6a36e284a2ab80
Source dataset
uspto-grants-2001_10
Patent number
US06310217B1

Reaction notes

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