HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 68724674, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1-Isopropylpiperidin-4-ol | HCID 79681 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | Ethyl 5-hydroxybenzofuran-2-carboxylate | HCID 22228632 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68724674 | HCID 68724674 | 56.4% |
Reaction Steps
The above prepared 5-hydroxy-benzofuran-2-carboxylic acid ethyl ester (1.50 g, 7.27 mmol) was dissolved in 36 mL of THF and treated successively at 10° C. with 1-isopropyl-piperidin-4-ol (1.46 g, 1.4 eq.), triphenylphosphine (2.67 g, 1.4 eq.) and DIAD (2.00 mL, 1.4 eq.), and the mixture then kept at ambient temperature for another 3 h. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, NEt3/AcOEt=2/98), yielded finally 1.36 g of the title compound as light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07534788B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-2ba38cdcd9f242a29ee9de5842be3c37 |
| Source note | uspto-grants-2009_05 |