HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Benzyl (2E)-3-(4-(benzyloxy)-2-(5,5-bis(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)phenyl)acrylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzyl acrylate | HCID 75617 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Dimethyl 2,2'-(3-(5-(benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetate | HCID 118292777 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | Benzyl (2E)-3-(4-(benzyloxy)-2-(5,5-bis(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)phenyl)acrylate | HCID 131736835 | 65.8% |
Reaction Steps
A mixture of dimethyl 2,2′-(3-(5-(benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetate (1.00 g), benzyl acrylate (1.021 g), palladium acetate (II) (0.047 g), tris(2-methylphenyl)phosphine (0.128 g), triethylamine (0.878 mL), and DMA (7.5 mL) was stirred at 130 C for 2 hours under microwave irradiation under an argon atmosphere. To the reaction mixture, water was added, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (0.770 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09428470B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-0751f1aa93084a1995cf21a57ae287e3 |
| Source note | uspto-grants-2016_08 |