Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | HCID 67252189 | HCID 67252189 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58292699 | HCID 58292699 | 67.7% |
Reaction Steps
To a solution of ethyl-2-(1-hydroxy-4-methoxy-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.35 g, 1.0 mmol) in THF (10 mL) was added dropwise concentrated hydrochloride acid (0.2 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hr and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc/PE=1/2) to give the title compound as a light yellow solid (180 mg, Y: 67.7%). 1H NMR (400 MHz, DMSO-d) δ 9.45 (s, 1H), 9.15 (s, 1H), 6.65-6.66 (d, J=1.2 Hz, 1H), 6.48-6.49 (d, J=1.2 Hz, 1H), 5.33-5.36 (m, 1H), 4.05-4.10 (m, 2H), 3.76 (s, 3H), 3.10-3.13 (m, 1H), 2.15-2.21 (m, 1H), 1.16-1.20 (m, 3H). MS (ESI) m/z=267 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08343944B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-3cbcf78f4e7241129d4b97da4c86d287 |
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| Source note | uspto-grants-2013_01 |
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