HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 7-Hydroxymethyl-4-phenylcoumarin
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 15780556 | HCID 15780556 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 7-Hydroxymethyl-4-phenylcoumarin | HCID 15780557 | — |
Reaction Steps
To a solution of 4-phenyl-7-coumarincarboxylic acid from Step 4 (550 mg) and Et3N (560 μL) in THF (25 mL) at 0° C. was added isobutylchloroformate (560 μL) dropwise. After 45 min., NaBH4 (185 mg) in H2O was added and stirring continued for a further 20 min. The mixture was poured onto 1N HCl, extracted 3×Et2O, dried and evaporated. Chromatography on silica gel using hexane/EtOAc 1:1 afforded the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05424320 |
| Source dataset | uspto-grants-1995_06 |
| ORD ID | ord-7f41e9a9881f4fde83ac8ce21e15cca1 |
| Source note | uspto-grants-1995_06 |