HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → (R)-4-methyl-4-(6-(4-(trifluoromethyl)cyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| 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 | — |
| Product | (R)-4-methyl-4-(6-(4-(trifluoromethyl)cyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one | HCID 67412717 | — |
Reaction Steps
(R)-4-(6-Hydroxynaphthalen-2-yl)-4-methyl-oxazolidin-2-one (0.1042 g, 0.0004284 mol) was dissolved in tetrahydrofuran (5.00 mL, 0.0616 mol) in a capped 40 mL vial. 4-Trifluoromethylcyclohexanol (0.101 g, 0.000600 mol) was added, followed by triphenylphosphine (0.180 g, 0.000685 mol) and the mixture was refluxed for 5 minutes. Diisopropyl azodicarboxylate (0.135 mL, 0.000685 mol) was then added and the mixture was heated at reflux overnight. TLC analysis showed that the reaction was complete. The mixture was concentrated to dryness under vacuum and purified by flash chromatography (0-20% EtOAc in methylene chloride).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546359B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-adf15315814143978acc26837659686a |
| Source note | uspto-grants-2013_10 |