Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethylene Oxide | HCID 6354 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 7-Hydroxyindole | HCID 2737651 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 22036415 | HCID 22036415 | 34% |
Reaction Steps
A mixture of 7-hydroxyindole (1.00 g, 7.51 mmol) and ethylene oxide (0.33 g, 7.50 mmol) in dioxane (3 mL) was placed in a reaction tube. NaH (60% in oil; 0.100 g, 2.45 mmol) was added and the reaction mixture was stirred at 100° C. for 5 days. The reaction mixture was poured into water, extracted with EtOAc, dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel using toluene/EtOAc (1:1) as eluent to give 0.45 g (34%) of the title product. Pos-EI-MS shows M+ and 5 ions supporting the stated structure. HRMS m/z calcd for C10H11NO2 (M)+ 177.0790, found 177.0799.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06465467B1 |
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| Source dataset | uspto-grants-2002_10 |
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| ORD ID | ord-20e35f2a640a462db4c25d33307ed197 |
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| Source note | uspto-grants-2002_10 |
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