Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Hydrofluoric Acid | HCID 14917 | — |
| Reactant | 5-(Tert-butyl-dimethyl-silanyloxy)-2-[4-(tert-butyl-dimethyl-silanyloxy)-3-fluoro-phenyl]-7-vinyl-benzooxazole | HCID 59741638 | — |
| Solvent | Water | HCID 962 | — |
| Product | Prinaberel | HCID 656954 | 88.5% |
Reaction Steps
Hydrofluoric acid (48 wt. % in water, 1 mL) was added into a solution of 5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-fluorophenyl)-7-vinyl-1,3-benzoxazole (1.5 g, 3.0 mmol), THF (6 mL) and acetonitrile (3 mL). The reaction mixture was stirred at 65° C. for 8 h, and then poured into water. The precipitated solid was filtered off and dried. Crystallization of the product from acetone/ethyl ether gave a white solid (0.72 g, 81% yield, m.p. 249-251° C.); MS m/e 272 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06794403B2 |
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| Source dataset | uspto-grants-2004_09 |
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| ORD ID | ord-bf261d8c914a474eb6cebb22e8770f87 |
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| Source note | uspto-grants-2004_09 |
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