HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-(3-Chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Ethyl 4-(3-chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylate | HCID 58064795 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(3-Chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylic acid | HCID 58064798 | — |
Reaction Steps
1.05 g (2.84 mmol) of the compound from Example 11A are provided in 30 ml of tetrahydrofuran, and 0.68 g (28.4 mmol) of lithium hydroxide and 10 ml of water are added at room temperature. The mixture is stirred at room temperature overnight, a 1N aqueous HCl solution is then added until an acidic pH is established, the mixture is extracted with ethyl acetate and the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated. The crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 0.60 g (62% of theory) of the title compound are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324268B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-46d158c42a2b48838d1998c0095c319d |
| Source note | uspto-grants-2012_12 |