Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 22734272 | HCID 22734272 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 12110025 | HCID 12110025 | 17.6% |
Reaction Steps
Under an argon atmosphere, a solution (2.6 ml) of Compound 142b (0.1 g) obtained in Step B in THF was cooled to −78° C., and then a 1.7M solution (0.2 ml) of n-butyl lithium in hexane was dropwise added thereto, followed by stirring at the same temperature for one hour. The reaction solution was adjusted to pH 7 by adding dropwise 1N hydrochloric acid, followed by stirring at room temperature for one hour. A small amount of water was added to the reaction solution and the mixture was extracted with ether. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2) to give Compound 142 (0.014 g, 17.4%) as pale-yellow crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06716987B1 |
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| Source dataset | uspto-grants-2004_04 |
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| ORD ID | ord-acac9a9dacd24eb295a6703623ed0fb5 |
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| Source note | uspto-grants-2004_04 |
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