HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 1,1-Dimethylethyl 2,5-dihydro-3-furancarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | 1,1-Dimethylethyl tetrahydro-4-hydroxy-3-furancarboxylate | HCID 11412816 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1,1-Dimethylethyl 2,5-dihydro-3-furancarboxylate | HCID 11206018 | 51.34% |
Reaction Conditions
| Temperature | 2.5 °C |
|---|
Reaction Steps
The product of Step B, t-butyl 4-hydroxytetrahydrofuran-3-carboxylate (0.83 g, 4.41 mmol) and PPh3 (1.74 g, 6.63 mmol) were placed in THF (5 mL), the solution was cooled to 0-5° C., and DIAD (1.13 mL, 5.74 mmol) was added dropwise. After reacting at rt for 12 h, the reaction mixture was filtered, washed with a solution of EtOAc/Hex=1/4, and the filtrate concentrated in vacuo The residue was purified by column chromatography (eluent, EtOAc/Hex=1/7) to give the title compound (0.39 g, 51.34%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07879852B2 |
| Source dataset | uspto-grants-2011_02 |
| ORD ID | ord-691e1cfd71c24767b82416dafd604112 |
| Source note | uspto-grants-2011_02 |