Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | HCID 67284846 | HCID 67284846 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 67285202 | HCID 67285202 | 81.6% |
Reaction Steps
To a solution containing ethyl 3-(5-nitro-2-phenyl-1H-indol-1-yl)propanoate (prepared as described in example 1g) (2.1 g; 6.2 mmol) in THF (20 ml) sodium borohydride (0.98 g, 24.8 mmol) and EtOH absolute (25 ml) were added; the reaction mixture was left under stirring at room temperature for 18 hours. Then water (5 ml) and HCl 2N were added to pH 6. The solution was transferred into a separating funnel, and extracted with ethyl acetate (2×50 ml). The organic phases were combined, and dried over Na2SO4. The solvent was removed by evaporation under reduced pressure and the residue was purified by flash chromatography on silica gel (n-hexane/EtOAc, n-hexane 100→70%) to give 3-(5-nitro-2-phenyl-1H-indol-1-yl)propan-1-ol (1.5 g), which was used without any further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399477B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-734a08e1ca4c419f884dbc6fa48fc714 |
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| Source note | uspto-grants-2013_03 |
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