HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl 3-(5-(benzyloxy)-2-(cyclohex-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate → tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(2-cyclohexyl-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl 3-(5-(benzyloxy)-2-(cyclohex-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate | HCID 118292887 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(2-cyclohexyl-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate | HCID 118292862 | 54.6% |
Reaction Steps
A mixture of tert-butyl 3-(5-(benzyloxy)-2-(cyclohex-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (118 mg), 10% Pd/C (containing about 55% water, 15 mg), and THF (2 mL) was stirred overnight at room temperature under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (54.1 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09428470B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-625a0e2e86e247ffae477272d4e57236 |
| Source note | uspto-grants-2016_08 |