Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ethyl 5,5-Dimethyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate | HCID 58539987 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 58540128 | HCID 58540128 | 106.8% |
Reaction Steps
A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 8 (310 mg, 1.30 mmol), THF (2 mL) and ethanol (2 mL). A solution of lithium hydroxide (125 mg, 5.21 mmol) in water (2 mL) was added, and the mixture was stirred at 50° C. for 2 h. After this time, the organic solvents were removed under reduced pressure, water (6 mL) was added, and the pH was adjusted to 3.0 with 2 N hydrochloric acid. The resulting suspension was filtered and the filter cake washed with water (2 mL). The filter cake was dried to constant weight under vacuum at 40° C. to afford a 100% yield (292 mg) of 9 as a white solid: mp 124-125° C.; 1H NMR (500 MHz, CDCl3) δ 7.93 (s, 1H), 3.10 (s, 2H), 1.34 (5, 6H); MS (ESI+) m/z 211.0 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08598174B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-12a8a035669e4f2cbd5c758c4c700b90 |
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| Source note | uspto-grants-2013_12 |
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