Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 131736720 | HCID 131736720 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 78128152 | HCID 78128152 | 72% |
Reaction Steps
Compound 14a (70 mg, 0.85 mmol) was dissolved in dried tetrahydrofuran (5 mL), cooled to 0° C. NaH (51 mg, 1.28 mmol) was added, and after its completion, the reaction mixture was raised to room temperature, and then raised to 50° C. to react for 4 hrs. The reaction was monitored by TLC (petroleum ether/ethyl acetate=8/1). After the reaction completed, water was added, and the mixture was extracted with ethyl acetate. The organic phase was combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate. Column chromatography (petroleum ether/ethyl acetate=5/1) afforded 150 mg of white solid (compound 14b), yield 72%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09416144B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-21470a7d23354deb94c0884fa4146e7b |
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| Source note | uspto-grants-2016_08 |
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