HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → Methyl 1-(benzo[d]oxazol-2-yl)cyclopropanecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | Methyl 1-((2-hydroxyphenyl)carbamoyl)cyclopropanecarboxylate | HCID 68513898 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 1-(benzo[d]oxazol-2-yl)cyclopropanecarboxylate | HCID 68518116 | 98% |
Reaction Steps
To a stirred suspension of methyl 1-((2-hydroxyphenyl)carbamoyl)cyclopropanecarboxylate (0.147 g, 0.62 mmol) in 2.5 mL THF at room temperature under nitrogen was added triphenylphosphine (0.361 g, 1.375 mmol) followed by DIAD (0.2663 ml, 1.375 mmol). After 2 hours, the reaction mixture was loaded directly onto a Biotage 40S column in THF and was eluted with 9/1 hexanes/EtOAc to provide the desired product as a yellow oil (132 mg, 97%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07723330B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-ee6bd76e89ff4c8390a0cdbb0b2c345d |
| Source note | uspto-grants-2010_05 |