HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Methyl 4-{(3E)-4-{2-[(4-tert-butyl-2-chlorobenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Chloro-4-(tert-butyl)benzyl bromide | HCID 57831334 | — |
| Reactant | HCID 57831366 | HCID 57831366 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Methyl 4-{(3E)-4-{2-[(4-tert-butyl-2-chlorobenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate | HCID 57831384 | — |
Reaction Steps
A solution of 450 mg (1.09 mmol) of methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-en-1-yl)benzoate in 10 ml of dry acetonitrile is mixed with 825.2 mg (1.64 mmol) of 2-chloro-4-(tert-butyl)benzyl bromide and 453.4 mg (3.28 mmol) of anhydrous potassium carbonate and heated under reflux for 12 h. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The resulting crude product is purified by preparative HPLC. 518 mg (0.87 mmol, 73.9% of theory) of a colorless foam are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08183271B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-107127d7fb91432bae58eba1bf1a2973 |
| Source note | uspto-grants-2012_05 |