HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 67491973, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | Methyl 3-hydroxyisoxazole-5-carboxylate | HCID 2724585 | — |
| Reactant | (3-Butyl-5-methyl-isoxazol-4-yl)-methanol | HCID 66599297 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67491973 | HCID 67491973 | 55% |
Reaction Steps
To a solution of 3-butyl-5-methyl-4-isoxazolyl-methanol (1.5 g, 8.9 mmol) in THF (30 mL) was added 3-oxo-2,3-dihydro-isoxazole-5-carboxylic acid methyl ester (1.27 g, 8.9 mmol) and triphenylphosphine (2.79 g, 10.6 mmol) at 0° C. under an argon atmosphere. Then diethyl azodicarboxylate (˜40% in toluene, 4.25 mL, 9.8 mmol) was added and the reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1) afforded the title compound (1.44 g, 55%) as a colourless liquid. MS: m/e=295.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173652B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-470bf4b17c9841859c1da77e41f16449 |
| Source note | uspto-grants-2012_05 |