Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Trimethylsilyl iodide | HCID 85247 | — |
| Reactant | HCID 90272380 | HCID 90272380 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | HCID 69702067 | HCID 69702067 | 63.6% |
Reaction Steps
Into a glass vial, the product from step (a) (0.126 mmol) in CHCl3 (3 ml) was placed. To this stirred solution, TMSI (172 μL, 1.26 mmol) was added. The reaction mixture was heated to 60° C. for 3 h. The reaction mixture was allowed to cool to room temperature and methanol (1 ml) was added to quench. The solvent was evaporated in vacuo to give the crude product as a yellow residue. The crude product was purified by semi-prep RP-HPLC to give the title compound as light yellow oil (15 mg). Recovered as acetate salt: 1H NMR (CDCl3) δ 7.18 (bs, 2H), 7.02 (d, J=7.2 Hz, 1H), 6.92 (d, J=7.2 Hz, 1H), 3.15-3.05 (m, 8H), 2.94-2.84 (m, 4H), 2.12-2.02 (m, 2H) 1.98 (s, 3H); MS: ESI (positive): 188 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09284277B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-dbfc0af1a8214606943703dea21f3989 |
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| Source note | uspto-grants-2016_03 |
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