HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl methyl ether → 3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-butan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | Lithium hydride | HCID 62714 | — |
| Reactant | 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-one | HCID 2758231 | — |
| Reactant | 1-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone | HCID 67430140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-butan-1-one | HCID 67429131 | 56.1% |
Reaction Steps
LiH (1.72 g) is added to a solution of 3′,5′-dichloro-2,2,2-trifluoroacetophenone (26.6 g) and 1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone (18.2 g) in THF (100 ml). After 30 minutes at 60° C. MTBE is added (200 ml) and the reaction mixture is poured onto water (30 ml) at 5° C. The organic phase is extracted with water and a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield 3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-butan-1-one (20.7 g). The crude product is used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08383659B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-d66b41011a8a4fc48eeafc8bfa0112b9 |
| Source note | uspto-grants-2013_02 |