HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | tert-Butyl 4-hydroxybenzoate | HCID 117640 | — |
| Reactant | Methyl 6-cyano-7-fluoro-2,2-dimethylchroman-4-carboxylate | HCID 67080271 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | Methyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-cyanochroman-4-carboxylate | HCID 67080240 | 32.8% |
Reaction Conditions
| Temperature | 110 °C |
|---|
Reaction Steps
Methyl 6-cyano-7-fluorochroman-4-carboxylate (from Example 3, Step E) (700 mg, 2.98 mmol), tert-butyl 4-hydroxybenzoate (578 mg, 2.98 mmol) and K2CO3 (494 mg, 3.57 mmol) were diluted with N-methylpyrrolidone (6 mL) and bubbled with argon for 10 minutes. The reaction was heated to 110° C. and stirred for 5 hours. The reaction was loaded directly onto a Biotage 40M cartridge and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield the title compound (400 mg, 32.8% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08716498B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-a8dafba262474963b17b054b87ceeec6 |
| Source note | uspto-grants-2014_05 |