Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | HCID 23031107 | HCID 23031107 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 21110582 | HCID 21110582 | 34.8% |
Reaction Steps
To a solution of ethyl 6-(7-amino-5-methylindan-4-yloxy)-2-acetyl-3-hydroxybenzoate (213 mg) in tetrahydrofuran (15 mL) were added lithium borohydride (390 mg) and ethanol (5 mL). The mixture was stirred at 60° C. for 4 days. To the reaction mixture was added water (10 mL). The mixture was acidified with an 10% aqueous solution of citric acid. To the mixture was added ethyl acetate (20 mL). The reaction mixture was stirred for 1 hour, and extracted with ethyl acetate (×3). The combined organic layers were washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=1/1) to give the title compound (66 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07230031B2 |
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| Source dataset | uspto-grants-2007_06 |
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| ORD ID | ord-21e633383c124e3dab3a2fa2789fb626 |
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| Source note | uspto-grants-2007_06 |
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