Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Benzyl chloromethyl ether | HCID 137983 | — |
| Reactant | HCID 66670204 | HCID 66670204 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66670221 | HCID 66670221 | — |
Reaction Steps
A 500 mg portion of benzyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate was dissolved in 10 ml of tetrahydrofuran, and 79 mg of sodium hydride (55% dispersion in oil) was added under ice-cooling, followed by stirring at room temperature for 30 minutes. A 0.357 ml portion of benzyl chloromethyl ether was added dropwise to this solution under ice-cooling, followed by stirring at room temperature for 1.5 hours. After adding water under ice-cooling, extraction was carried out with ethyl acetate. Then, after washing with saturated brine and then drying with anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:8) to obtain 503 mg of benzyl 1-[(benzyloxy)methyl]-2-methyl-5-phenyl-1H-pyrrole-3-carboxylate as a colorless liquid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08222274B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-f4d32a46369640008ded0a07c3496e09 |
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| Source note | uspto-grants-2012_07 |
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