Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 4,4-Dimethylaminopyridine | HCID 86589049 | — |
| Reactant | Poly[oxy[(1S)-1-methyl-2-oxo-1,2-ethanediyl]], α-hydro-ω-(2-propyn-1-yloxy)- | HCID 86651912 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 54180109 | HCID 54180109 | 85.3% |
Reaction Steps
19.96 g (156 mmol) of the obtained 2-propynyl 2-hydroxypropionate, 7.17 g (156 mmol) of formic acid, and 15.23 g (125 mmol) of 4,4-dimethylaminopyridine (nucleating agent) were dissolved in 100 g of 1,2-dichloroethane (solvent), and a mixed solution of 35.35 g (171 mmol) of N,N′-dicyclohexylcarbodiimide (dehydrating agent) and 50 g of 1,2-dichloroethane was added thereto at 10° C., taking 30 minutes. These were reacted at room temperature for 4 hours, and the absence of the starting materials was confirmed through gas chromatography. Subsequently, the reaction liquid was filtered to remove N,N′-dicyclohexylurea, and the filtrate was concentrated. The concentrate was purified through silica gel column chromatography, and from the fraction taken with hexane/ethyl acetate=4/1, 20.78 g (yield 85%) of 2-propynyl 2-(formyloxy)propionate was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08580429B2 |
|---|
| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-562381b6848f4ce7b99db1c8b213ae7b |
|---|
| Source note | uspto-grants-2013_11 |
|---|