Hydrochloric Acid → HCID 71660985, compound

HRID 1506836Notes

Reaction equation

HRID 1506836 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=[O:20])[C:18]=2[OH:19])=[C:15]([OH:21])[CH:14]=[C:13]([OH:22])[C:12]=3[CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[CH:5][CH:4]=1.[C:30](=O)([O-])[O-].[Cs+].[Cs+].C(Br)C=C(C)C.Cl>O>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:16]([C:17](=[O:20])[C:18]=2[O:19][CH3:30])=[C:15]([OH:21])[CH:14]=[C:13]([OH:22])[C:12]=3[CH2:23][CH:24]=[C:25]([CH3:26])[CH3:27])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 716211673,5,7-Trihydroxy-8-(3-methyl-but-2-enyl)-2-(4-trifluoromethyl-phenyl)-chromen-4-one

Product 1

HCID 71660985HCID 71660985, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. additionwas dropped into the solution under icewater bath condition
  2. extractionThe solution was extracted with ethyl acetate for 2 times
  3. washwashed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationAfter filtration, crude product
  6. washwas eluted with ethyl acetate/petroleum through silica gel column

Sources & evidence

ORD record
ord-24caa240896b46cab5bdcad5f3153309
Source dataset
uspto-grants-2015_12
Patent number
US09221781B2

Reaction notes

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