Cesium fluoride → HCID 22252387, compound

HRID 1611993Notes

Reaction equation

HRID 1611993 reaction equation
C([Si](C(C)C)(C(C)C)[S:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1)(C)C.[F-].[Cs+].Br[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C)C=O>[CH3:13][O:12][C:10]1[CH:11]=[C:6]([S:5][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:7]=[C:8]([O:16][CH3:17])[C:9]=1[O:14][CH3:15]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 76300Ethyl 4-bromobutyrateHCID 22252390HCID 22252390, compound

Product 1

HCID 22252387HCID 22252387, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.78 g of the compound obtained in Step A, 0.835 g of CsF and 1.1 g of ethyl 4-bromobutyrate in 80 ml of dimethylformamide is stirred, under argon, for 3 hours. After removal of the solvent by distillation, the residue is taken up in a mixture of water/dichloromethane, decanted and then dried over sodium sulphate. Chromatography over silica gel eluted with dichloromethane enables the expected product to be isolated.

Workup

  1. customAfter removal of the solvent
  2. distillationby distillation
  3. additionthe residue is taken up in a mixture of water/dichloromethane
  4. customdecanted
  5. dry with materialdried over sodium sulphate
  6. washChromatography over silica gel eluted with dichloromethane
  7. customto be isolated

Sources & evidence

ORD record
ord-d2af4b1546184b3faaf541048fde1b03
Source dataset
uspto-grants-2006_01
Patent number
US06992085B2

Reaction notes

Loading…