HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium sulfate decahydrate → {4-[((3-Methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]phenyl}methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium sulfate decahydrate | HCID 62649 | — |
| Reactant | Methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoate | HCID 23157327 | — |
| Reactant | Diisobutylaluminumhydride toluene | HCID 86583787 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | {4-[((3-Methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]phenyl}methanol | HCID 23157500 | 75.4% |
Reaction Steps
To a solution of methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoate (1.34 g, 2.90 mmol) in tetrahydrofuran (10 mL) was added dropwise 1.0 M diisobutylaluminum hydride toluene solution (6.38 mL, 6.38 mmol) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, sodium sulfate decahydrate was added and the mixture was further stirred at room temperature for 1 hr. The insoluble material was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90-60/40) to give the title compound (950 mg, yield 75%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07786165B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-3b77d3dbc0854d6ebb249426aaa7b994 |
| Source note | uspto-grants-2010_08 |