Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Cyanomethylenetributylphosphorane | HCID 4622928 | — |
| Reactant | HCID 86701441 | HCID 86701441 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86701479 | HCID 86701479 | — |
Reaction Steps
4-Allyl-7-methyl-1H-indol-5-ol (Example 1-C) (2.77 g, 14.79 mmol) was dissolved in toluene (74.0 mL) and methanol (0.599 mL, 14.79 mmol) was added followed by cyanomethylenetributylphosphorane (8.93 g, 37.0 mmol). The reaction was heated at 110° C. for 1 hour. The reaction was cooled to room temperature and then concentrated. The residue was then absorbed onto silica and purified by silica gel flash chromatography (0-50% ethyl acetate/heptanes) to provide the title compound. MS (ESI+) m/z 202.17 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09056874B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-bc77a7fa17034b2eb8795bf6cb9cb811 |
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| Source note | uspto-grants-2015_06 |
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