HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → (E)-3-Cyclopentyl-2-(4-methylsulfanyl-phenyl)-acrylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Methylthio)phenylboronic acid | HCID 2733959 | — |
| Reactant | (Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl ester | HCID 86605124 | — |
| Catalyst | HCID 178420553 | HCID 178420553 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | (E)-3-Cyclopentyl-2-(4-methylsulfanyl-phenyl)-acrylic acid ethyl ester | HCID 67084466 | 85.6% |
Reaction Steps
Following the method of example 54c, reaction of (Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl ester (56.8 g, 229 mmol) with 4-(methylthio)benzene boronic acid (46.3 g, 276 mmol) and tetrakis(triphenylphosphino)palladium(0) (10.4 g, 3 mol %) in a mixture of toluene (1600 ml), ethanol (421 ml) and 2 M aqueous sodium carbonate solution (420 ml) affords the title compound as an oil (56.9 g). MS (m/e): 291.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576108B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-4a9414ef3126464ca37721e63a51bc71 |
| Source note | uspto-grants-2009_08 |