HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetone → 3-[N-[5-Chloro-3-(alpha-hydroxy-2-chlorobenzyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | Cesium trichloride | HCID 20975861 | — |
| Reactant | 3-[N-[5-chloro-3-(2-chlorobenzoyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester | HCID 70277444 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 3-[N-[5-Chloro-3-(alpha-hydroxy-2-chlorobenzyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester | HCID 70277553 | 103.8% |
Reaction Steps
To a solution of 3-[N-[5-chloro-3-(2-chlorobenzoyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester (2.37 g) and cesium trichloride.heptahydrate (2.98 g) in methanol (100 ml) was gradually added, sodium borohydride (303 mg) at room temperature. The mixture stirred for 20 minutes at room temperature, to which was added acetone, then the solvent was distilled off. To the residue were added 1M potassium hydrogensulfate and acetic acid ethyl ester. The organic layer was washed with a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by means of a silica-gel column chromatography to give a non-crystalline solid (2.47 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05698691 |
| Source dataset | uspto-grants-1997_12 |
| ORD ID | ord-90c17bfe0b3a43ccac691f5f5ec84f75 |
| Source note | uspto-grants-1997_12 |