Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | Cyclopentanecarboxylic acid | HCID 18840 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | HCID 18971235 | HCID 18971235 | — |
Reaction Steps
480 mmol of butyllithium are added to 480 mmol of diisopropylamine in 600 ml of anhydrous tetrahydrofuran (THF), under argon, at -70° C. After stirring for 15 minutes at -70° C., 240 mmol of cyclopentanecarboxylic acid are added dropwise. After warming to room temperature, the mixture is heated for one hour at 50° C. The reaction medium is then cooled to -70° C. and 260 mmol of ethyl chloroformate are added. The solution is stirred for 20 minutes and then poured into ice-water. The medium is acidified with concentrated hydrochloric acid and then extracted with dichloromethane. The organic phase is then washed with water to neutral pH and then with saturated sodium chloride solution. After drying and evaporation, the expected product is obtained in the form of an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05814622 |
|---|
| Source dataset | uspto-grants-1998_09 |
|---|
| ORD ID | ord-a40983275556495bad7fa180049b1ab2 |
|---|
| Source note | uspto-grants-1998_09 |
|---|