HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 68726283, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1-Isopropylpiperidin-4-ol | HCID 79681 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | HCID 68725520 | HCID 68725520 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68726283 | HCID 68726283 | 119.7% |
Reaction Steps
The above prepared 6-hydroxy-3-isopropyl-benzofuran-2-carboxylic acid ethyl ester (0.400 g, 1.61 mmol) was dissolved in 8 mL of THF and treated successively at 0° C. with 1-isopropyl-piperidin-4-ol (0.461 g, 2 eq.), triphenylphosphine (0.845 g, 2 eq.) and DIAD (0.630 mL, 2 eq.), and the mixture then kept at ambient temperature for another 1 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, NEt3/AcOEt=5/95), yielded 0.720 g of the title compound as light yellow oil, contaminated with tiny amounts of reduced DIAD.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07534788B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-87f0d5cdc3704b898d6d87630fb1d157 |
| Source note | uspto-grants-2009_05 |