Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Phenoxyethanol | HCID 31236 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate | HCID 60155786 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 71278746 | HCID 71278746 | 53.5% |
Reaction Steps
A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.100 g, 0.287 mmol), 2-phenoxyethanol (0.0475 g, 0.344 mmol) and triphenylphosphine (0.113 g, 0.431 mmol) in THF (2 mL) was added with a solution of a 40% solution of diethyl azodicarboxylate in toluene (0.225 g, 0.517 mmol) in THF (0.5 mL), and the mixture was stirred at 70° C. for 3 hours in a sealed tube. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/ethyl acetate) to obtain tert-butyl 4-[(3-oxo-6-(2-phenoxyethoxy)-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.0720 g, 53%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09156827B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-e00bd6b151544a27820f08487513042f |
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| Source note | uspto-grants-2015_10 |
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