Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | HCID 24853387 | HCID 24853387 | — |
| Reactant | HCID 178418573 | HCID 178418573 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 24853388 | HCID 24853388 | 103.2% |
Reaction Steps
The title compound of Example 5.3 (739 mg, 3.9 mmol) was dissolved in THF (20 mL) under Argon and the flask was immersed in ice. Methyl magnesium bromide (1 M solution/diethyl ether 6.6 mL, 19.7 mmol) was added dropwise while the reaction was cooled in ice. After fifteen minutes at 0° C., the ice bath was removed and the reaction was allowed to stir at room temperature for two hours. Aqueous NH4Cl (saturated) was added to quench the reaction and an aqueous workup was done extracting with ethyl acetate three times. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (3% MeOH/DCM) to yield the title compound as a clear oil (818 mg, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07772235B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-febd3f2e16214d13bb68a454c8b4ad42 |
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| Source note | uspto-grants-2010_08 |
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