HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 87426500, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 2,2-Difluoroethan-1-ol | HCID 136187 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | Methyl 4-hydroxy-3-methylbenzoate | HCID 11240684 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 87426500 | HCID 87426500 | 91.7% |
Reaction Steps
To a stirred solution of methyl 4-hydroxy-3-methylbenzoate (1.5 g, 9.0 mmol), 2,2-difluoroethanol (0.90 g, 10.8 mmol), triphenylphosphine (3.6 g, 13.5 mmol) in THF (40 mL) is added dropwise diethyl azodicarboxylate (4.9 mL, 10.8 mmol, 40% solution in toluene) at 0° C. The mixture is stirred at rt for 30 minutes. Then the reaction mixture is stirred at 60° C. for 2 hours. After cooling to rt, the mixture is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (18:1) to give 1.9 g (90% yield) of the title compound as white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09187475B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-510c74c4a3e94ab4835db6f5013b3e1f |
| Source note | uspto-grants-2015_11 |