Cesium carbonate → HCID 68565082, compound

HRID 1593547Notes

Reaction equation

HRID 1593547 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7]([CH3:14])([CH3:13])[CH:6]=[C:5]2[C:15]([F:18])([F:17])[F:16].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27][CH2:28][OH:29]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:26][CH2:27][CH2:28][OH:29])[O:8][C:7]([CH3:14])([CH3:13])[CH:6]=[C:5]2[C:15]([F:16])([F:18])[F:17]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 123083-Bromo-1-propanolHCID 665248776-Chloro-2,2-dimethyl-4-(trifluoromethyl)-2H-1-benzopyran-7-ol

Product 1

HCID 68565082HCID 68565082, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-Chloro-2,2-dimethyl-4-(trifluoromethyl)-2H-chromen-7-ol (10 g, 36.23 mmol) in 150 mL DMF was added cesium carbonate (24.8 g, 76.11 mmol) followed by 3-bromo-1-propanol (7.6 g, 54.3 mmol) and the mixture stirred at ambient temperature for 24 h. Dilution with water followed by extraction with AcOE and washing the organic extracts with water, drying over anhydrous Na2SO4 and finally concentrating under reduced pressure gave crude alkylated product. Purification over silica gel using AcOEt/hexanes provided the desired 3-((6-chloro-2,2-dimethyl-4-(trifluoromethyl)-2H-chromen-7-yl)oxy)propan-1-ol (9.5 g, 78%).

Workup

  1. extractionDilution with water followed by extraction with AcOE
  2. washwashing the organic extracts with water
  3. dry with materialdrying over anhydrous Na2SO4
  4. concentrationfinally concentrating under reduced pressure
  5. customgave crude alkylated product
  6. customPurification over silica gel

Sources & evidence

ORD record
ord-3c05fd3d5c704a03940da4e097cb4120
Source dataset
uspto-grants-2007_11
Patent number
US07297715B2

Reaction notes

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