Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pentane | HCID 8003 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one | HCID 22935595 | — |
| Reactant | HCID 178418306 | HCID 178418306 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66759808 | HCID 66759808 | 33% |
Reaction Steps
A pentane solution (2.00 mL, 3.08 mmol) containing 1.54 M t-butyllithium was added dropwise to a solution of THF (4 mL) containing 5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one (800 mg, 2.03 mmol) synthesized in Reference Example 42 under argon atmosphere at −70° C. or lower, and then the mixture was warmed to 0° C. The reaction solution was stirred under ice-cooling condition for 30 minutes, and then water was added thereto and extraction was performed using ethyl acetate. The organic layer was washed with water and saturated saline, and then dried using anhydrous sodium sulfate. It was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane-ethyl acetate 100:0 to 8:1) and silica gel column chromatography (hexane-ethyl acetate 100:0 to 8:1), and after that, crystallization was performed using hexane to give 300 mg of the title compound (yield: 33%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08957069B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-8b0ec38517784f8b9fa5054ae4f6a8b4 |
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| Source note | uspto-grants-2015_02 |
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