HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → (R)-4-methyl-4-(6-(4-(trifluoromethyl)cyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | 4-(Trifluoromethyl)cyclohexan-1-ol | HCID 2779765 | — |
| Reactant | (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one | HCID 51066623 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (R)-4-methyl-4-(6-(4-(trifluoromethyl)cyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one | HCID 67412717 | — |
Reaction Steps
In a 40 mL vial, 4-trifluoromethyl-cyclohexanol (713.2 mg, 0.004241 mol) was diluted with tetrahydrofuran (19.0 mL), then (R)-4-(6-hydroxy-naphthalen-2-yl)-4-methyl-oxazolidin-2-one (0.9462 g, 0.003890 mol) and triphenylphosphine (1.3031 g, 0.0049682 mol) were added. The mixture was stirred and then diisopropyl azodicarboxylate (0.91 mL, 0.0046 mol) was added. The reaction was stirred at room temperature for 38 h. The reaction mixture was concentrated in vacuo, taken up in DCM, adsorbed onto silica gel and chromatographed (0-100% EtOAc/Hexanes). Isolated was 223.5 mg (15%) of product as cis/trans mixture.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546359B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-634278de22c040ddb4a64c9a3d4a7490 |
| Source note | uspto-grants-2013_10 |