Hydrochloric Acid → benzyl 4-(1H-indol-3-yl)butanoate

HRID 1974551Notes

Reaction equation

HRID 1974551 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:14])=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 8617Indole-3-Butyric AcidHCID 11430Potassium Carbonate

Product 1

HCID 1482096benzyl 4-(1H-indol-3-yl)butanoateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-indolebutyric acid (25 g) and potassium carbonate (20 g) in dimethylformamide (150 ml) was added benzylbromide (21 g) at room temperature. After stirring for 4 hours, the mixture was poured into ice and diluted hydrochloric acid (300 ml). The organic layer was extracted with ethyl acetate (150 ml), and the extract was washed with water (150 ml×3) and dried over magnesium sulfate. After the solvent was removed in vacuo, the residue was crystallized from n-hexane to give a solid of benzyl 4-(3-indolyl)butyrate (33.9 g).

Workup

  1. extractionThe organic layer was extracted with ethyl acetate (150 ml)
  2. washthe extract was washed with water (150 ml×3)
  3. dry with materialdried over magnesium sulfate
  4. customAfter the solvent was removed in vacuo
  5. customthe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-0a00b4a574234698b32465914e367558
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

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