Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 89404248 | HCID 89404248 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | HCID 89401938 | HCID 89401938 | 44.8% |
Reaction Steps
In a 50 mL, 3N round-bottomed flask equipped with nitrogen inlet, thermometer pocket and stopper, (Z)-isopropyl 3-(4-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazol-1-yl)acrylate (2) (1.0 g, 1.0 eq.) was dissolved in THF: H2O (20 mL, 1:1, 20V). To this reaction mixture LiOH.H2O (0.535 g, 5.0 eq.) was added at 0° C. This reaction mixture was stirred for 3-4 h and progress of the reaction was followed by TLC using 20% ethyl acetate/n-hexane as mobile phase. Reaction mixture was acidified using dilute HCl. The reaction mixture was extracted with EtOAc (3×20 mL). The combined organic layers was washed with brine solution (3×50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure by rotary evaporation to afford 0.4 g of crude compound which was used for next step without purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428490B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-85b0d052a5174ca6bf771db5733251e2 |
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| Source note | uspto-grants-2016_08 |
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