Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Malonic Acid | HCID 867 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | 1-Benzothiophene-3-carbaldehyde | HCID 227328 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 58043931 | HCID 58043931 | 89% |
Reaction Steps
A suspension of benzo[b]thiophene-3-carbaldehyde (4.9 g, 30 mol), malonic acid (6.6 g, 60 mmol) and piperidine (1 mL) in 100 mL anhydrous pyridine was heated at 110° C. for overnight. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was taken up in 100 mL of water and 1 N hydrochloric acid was added to adjust the pH of this solution to ca. 3. The resulting suspension was filtered and the yellow solid was collected, washed with water (3×30 mL) dried in vacuo to give 329a as a yellow solid (5.5 g, 89%). MS: [M+H]+ 205.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08618107B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-c392e72248b3486b82577a57a79194a8 |
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| Source note | uspto-grants-2013_12 |
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