Cesium fluoride → HCID 57849361, compound

HRID 736514Notes

Reaction equation

HRID 736514 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:26][CH3:27])([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[C:15]([CH3:25])[CH:14]=2)[CH2:11][CH3:12])=[CH:6][C:5]=1[CH3:28].[F-].[Cs+]>C(#N)C.O>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH2:11][CH3:12])([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[C:15]([CH3:25])[CH:14]=2)[CH2:26][CH3:27])=[CH:6][C:5]=1[CH3:28]

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 57849320HCID 57849320, compound

Product 1

HCID 57849361HCID 57849361, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To an ambient temperature suspension of 4-[1-Ethyl-1-(3-methyl-4-trimethylsilanylethynyl-phenyl)-propyl]-2-methyl-benzoic acid methyl ester (6.8 g, 16.72 mmol) in acetonitrile/water (180/30 ml) is added cesium fluoride (25.4 g, 167.2 mmol) and stirred for 3d. The reaction mixture is concentrated and partitioned between EtOAc (500 ml) and 1N HCl (200 ml). The aqueous phase is extracted with a second portion of EtOAc (200 ml) and the combined organic phases are washed with brine (200 ml), dried (MgSO4), concentrated and chromatographed (330 g SiO2, 1% EtOAc/Hexanes) to yield the title compound (5.52 g, 99%).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompartitioned between EtOAc (500 ml) and 1N HCl (200 ml)
  3. extractionThe aqueous phase is extracted with a second portion of EtOAc (200 ml)
  4. washthe combined organic phases are washed with brine (200 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customchromatographed (330 g SiO2, 1% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-08fc20395f2f4f16a565a4db0d58f258
Source dataset
uspto-grants-2009_09
Patent number
US07595345B2

Reaction notes

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