HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-chlorobutyrate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 4-Chlorobutyryl chloride | HCID 78370 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Methyl 6-hydroxy-2-oxohexahydro-3,5-methano-2h-cyclopenta-[b]furan-7-carboxylate | HCID 15601184 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-chlorobutyrate | HCID 57867100 | 96.1% |
Reaction Steps
In 180 ml of tetrahydrofuran were dissolved 21.2 g of methyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta-[b]furan-7-carboxylate and 16.9 g of 4-chlorobutyric acid chloride. To the solution below 20° C., 9.10 g of pyridine was added dropwise. The solution was stirred at room temperature for 1 hour and combined with 40 g of a 5% aqueous solution of sodium hydrogen carbonate, followed by ordinary work-up. There was obtained 30.4 g of a crude product (crude yield 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07833694B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-4456801942a345148fc2c7e28d5b2178 |
| Source note | uspto-grants-2010_11 |