Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Potassium bisulfate | HCID 516920 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | HCID 59829865 | HCID 59829865 | 62% |
Reaction Steps
Crude IM06-c (0.51 g) dissolved in anhydrous tetrahydrofuran (6 mL) was placed in a 50 mL two-neck flask under a nitrogen atmosphere, and after cooling to −78° C., a hexane solution of 1.59M n-butyllithium (1.1 mL, 1.76 mmol) was added dropwise. The reaction mixture was stirred for 1 hour, mixed with dry ice (7 g) and further stirred for 1 hour. The reaction mixture was adjusted to pH 2.5 by mixing with 10% potassium hydrogensulfate and extracted twice with ethyl acetate (40 mL). The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate. After filtration and evaporation, the residue was purified by silica gel column chromatography (hexane-ethylacetate=2:1) to obtain the title compound (IM07-c:0.28 g, yield 62%, 3 steps).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399464B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-61b8df46fb8243e7aa1e4146303f601d |
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| Source note | uspto-grants-2013_03 |
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