HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → HCID 22016838, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | Methyl 4-cyano-3-methoxybenzoate | HCID 22464400 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22016838 | HCID 22016838 | 87.2% |
Reaction Steps
To a solution of the ester from Step D (48.8 g, 255 mmol) in 400 mL of dry THF under argon at room temperature was added lithium borohydride (255 mL, 510 mmol, 2M THF) over 5 minutes. After 1.5 hours, the reaction was warmed to reflux for 0.5 hours, then cooled to room temperature. The solution was poured into EtOAc/IN HCl soln. [CAUTION], and the layers were separated. The organic layer was washed with water, sat Na2CO3 soln. and brine (4x), dried (Na2SO4), and concentrated in vacuo to provide the titled product (36.3 g, 87% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06103487 |
| Source dataset | uspto-grants-2000_08 |
| ORD ID | ord-c12ef83b1dd84ef79d675698d3364fd1 |
| Source note | uspto-grants-2000_08 |