Cesium carbonate → HCID 66884659, compound

HRID 241385Notes

Reaction equation

HRID 241385 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH3:9])=[CH:4][C:3]=1[C:10](=[O:29])[CH2:11][CH2:12][C:13]1[S:14][C:15]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:16]=2[C:17]=1[CH2:18][CH2:19][CH3:20].[C:30](=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][C:38]([O:40][CH3:41])=[O:39]>CC(C)=O>[OH:1][C:2]1[C:3]([C:10](=[O:29])[CH2:11][CH2:12][C:13]2[S:14][C:15]3[CH:24]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:22]=[CH:21][C:16]=3[C:17]=2[CH2:18][CH2:19][CH3:20])=[CH:4][C:5]([CH3:9])=[C:6]([CH:7]=1)[O:8][CH2:37][C:38]([O:40][CH2:41][CH3:30])=[O:39]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 66884222HCID 66884222, compound

Product 1

HCID 66884659HCID 66884659, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

In acetone (0.8 mL) was suspended 1-(2,4-dihydroxy-5-methylphenyl)-3-[3-propyl-6-(trifluoromethyl)benzothiophen-2-yl]propan-1-one and cesium carbonate (33 mg, 0.788 mmol). After addition of 1-Methyl bromoacetate in acetone (79 μL), the mixture was stirred for 7 hours at room temperature, diluted with ice-water, and extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. After the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate, 6:1) to give the titled compound as a pale yellow crystal (34 mg, yield 86%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter the solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate, 6:1)

Sources & evidence

ORD record
ord-1d25d34d62bd49bc919769af23571f89
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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