Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | Ethyl 5-hydroxypentanoate | HCID 12917181 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86682561 | HCID 86682561 | 179.1% |
Reaction Steps
Ethyl 5-hydroxypentanoate (1.12 g, 7.66 mmol) was dissolved in 25 mL of methylene chloride, triphosgene (772 mg, 0.34 equivalent), and pyridine (0.743 mL, 1.2 equivalent) were sequentially added while stirred at 0° C., and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, water was added, and extraction operation (methylene chloride) was performed. The separated organic layer was washed using an aqueous saturated sodium chloride solution, and dried with magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the crude product. This was purified by column chromatography (ethyl acetate:n-hexane=1:10) to obtain the title compound (972 mg) having the following physical property values.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09006246B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-a38eb0cbc66f43bf8ca5aabdc4c4077d |
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| Source note | uspto-grants-2015_04 |
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