HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 66699467, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-one | HCID 13295518 | — |
| Reactant | (S)-3-[(4-Iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile | HCID 57884505 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Product | HCID 66699467 | HCID 66699467 | 53.4% |
Reaction Steps
Stir a mixture of 1-(2-Hydroxy-4-mercapto-3-propyl-phenyl)-ethanone (250 mg, 1.18 mmol), (S)-3-[(4-Iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (515 mg, 1.18 mmol) and cesium carbonate (769 mg, 2.36 mmol) in 2-butanone (10 ml) at room temperature under argon for 24 hours. Pour the mixture into water (85 ml) and extract with ethyl acetate (3×25 ml). Combine the organic extracts and wash with water, brine, then dry over sodium sulfate, filter and concentrate. Purify the crude product via silica chromatography eluting with 1:4 ethyl acetate:hexanes to give the title compound (325 mg, 53%). MS (m/z) 514 (M−H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07816523B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-55c1720b73bc4d1fa67d16e75e57f400 |
| Source note | uspto-grants-2010_10 |