HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 71660985, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Butene, 1-bromo-3-methyl- | HCID 70092 | — |
| Reactant | 3,5,7-Trihydroxy-8-(3-methyl-but-2-enyl)-2-(4-trifluoromethyl-phenyl)-chromen-4-one | HCID 71621167 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 71660985 | HCID 71660985 | 16.5% |
Reaction Steps
Intermediate 2-(4-trifluorophenyl)-3-methoxy-5,7-dihydroxy-4H-chrom-4-one (500 mg, 1.42 mmol) of compound 1 and cesium carbonate (4.95 g, 15 mmol) were dissolved into 25 mL water, and prenyl bromide (220 mg, 1.5 mmol) was dropped into the solution under icewater bath condition. After that, the solution was kept overnight under room temperature, and pH was adjusted about 6 with 2N hydrochloride. The solution was extracted with ethyl acetate for 2 times. Organic phases were combined, washed with saturated sodium chloride aqueous solution and dried with anhydrous sodium sulfate. After filtration, crude product was eluted with ethyl acetate/petroleum through silica gel column. Yellow target compound (95 mg, yield 16.5%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221781B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-24caa240896b46cab5bdcad5f3153309 |
| Source note | uspto-grants-2015_12 |