Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | HCID 68952924 | HCID 68952924 | — |
| Reactant | HCID 178418306 | HCID 178418306 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 10824737 | HCID 10824737 | 74.9% |
Reaction Steps
Dissolve 2-(4-chloro-phenyl)-4-methyl-thiophene (0.53 g, 1.85 mmol) in THF (25 mL) and cool to −78° C. Add t-BuLi (1.7 M, 2.3 mL, 3.88 mmol) dropwise. Stir the solution at −78° C. for 20 min. Cannulate the solution into a flask containing powdered dry ice (10 g). Stir the reaction and allow to warm to RT. Quench the reaction with saturated NH4Cl (10 mL), dilute with water (40 mL), and extract with EtOAc (2×50 mL). Dry the combined organic layers over Na2SO4, filter, and concentrate. Purify the crude material by washing with hexane (2×20 mL) to give 0.35 g (74%) of the title compound. LC-MS/ES m/z (35Cl) 251.0 [M−H]−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08263772B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-ddf293d19cfc43f6a3b0d5fb03254703 |
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| Source note | uspto-grants-2012_09 |
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