Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Diphosgene | HCID 10426 | — |
| Reactant | (4R)-4-phenyl-1,3-oxazolidin-2-one | HCID 730425 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 44138554 | HCID 44138554 | 65% |
Reaction Steps
To a solution of (R)-(−)-4-phenyl-2-oxazolidinone in THF (200 mL) at 0° C. was slowly added a 2.5 M solution of butyllithium in hexane (19 mL, 0.03 mol). The mixture was stirred at 0° C. for 30 min and then cooled to −78° C. Trichloromethyl chloroformate (7.8 mL, 0.03 mol) was added quickly in one portion and the reaction solution was stirred at −78° C. for 30 min. The resulting mixture was allowed to warm to room temperature, and was subsequently concentrated in vacuo. The resulting residue was taken up in CH2Cl2 (200 mL) and filtered, and the filtrate was concentrated in vacuo to afford the title compound as an off-white solid (4.5 g, 65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07517876B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-8828a17973d14b8fa91a82d0355454ac |
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| Source note | uspto-grants-2009_04 |
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