HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Thiocresol → 6-[(3-Methylphenyl)sulfanyl]-1,2,3,4-tetrahydronaphthalen-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Thiocresol | HCID 7930 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate | HCID 11098384 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 6-[(3-Methylphenyl)sulfanyl]-1,2,3,4-tetrahydronaphthalen-1-one | HCID 118597717 | 110% |
Reaction Steps
The suspension of 5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (1.8 g, 6.1 mmol), 3-methylbenzene-1-thiol (0.76 g, 6.1 mmol), Pd2(dba)3 (142 mg, 0.153 mmol), Xantphos (177 mg, 0.306 mmol) and DIEA (1.58 g, 12.2 mmol) in 1,4-dioxane (60 mL) was stirred at reflux overnight under N2. The reaction was filtered and concentrated. Purification by silica gel chromatography (PE:EtOAc=5:1) gave 1.8 g (100%) of the title compound as an orange oil. [M+H] Calc'd for C17H16OS, 269. Found, 269.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447046B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-728e7a341e764f538ab3f60ccd3d628b |
| Source note | uspto-grants-2016_09 |