Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloride | HCID 312 | — |
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 19603727 | HCID 19603727 | — |
| Reactant | Benzyl (1H-indol-3-yl)acetate | HCID 19603827 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 19603795 | HCID 19603795 | 43% |
Reaction Steps
A mixture of 4-tert-butyl-2-[5-(chloromethyl)benzofuran-2-yl]thiazole (0.30 g), benzyl indole-3-acetate (0.25 g), sodium hydroxide (0.24 g) and small amount of cetyl trymethylammonium chloride in dichloromethane (10 ml) was stirred under reflux for 3 hours. After water was added to the reaction mixture, the mixture was neutralized with diluted hydrochloric acid and the resulting mixture was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of dichloromethane and methanol. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}indole-3-acetic acid (0.18 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05994378 |
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| Source dataset | uspto-grants-1999_11 |
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| ORD ID | ord-f8b0191c799741488e3ce653ecaaf150 |
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| Source note | uspto-grants-1999_11 |
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