HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propargyl alcohol → (5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | (5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one | HCID 23626594 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one | HCID 58822464 | 105.1% |
Reaction Steps
(5R)-3-(3-Fluoro-4-iodophenyl)-5-(azidomethyl)oxazolidin-2-one (10 g, 28 mmol) was dissolved in acetonitrile (80 mL). Propargyl alcohol (3.2 mL, 56 mmol) was added and then CuI (526 mg, 2.8 mmol) and it was stirred overnight. The solidified reaction mixture was extracted with ethyl acetate/acetonitrile, washed with water and dried over magnesium sulfate. Evaporation of solvent under vacuum gave 12.3 g crude product (quantitative).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07498350B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-de891f7c262a4a0481ecf8d5394091e6 |
| Source note | uspto-grants-2009_03 |