Cesium fluoride → HCID 17747369, compound

HRID 1715355Notes

Reaction equation

HRID 1715355 reaction equation
[C:1]1([C:7]2[S:8][C:9]([CH:12]=[O:13])=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[Cs+].[C:16]([Si](C)(C)C)([F:19])([F:18])[F:17]>COCCOC>[F:17][C:16]([F:19])([F:18])[C:12]([C:9]1[S:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:11][CH:10]=1)=[O:13]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 27637062-Phenyl-1,3-thiazole-5-carbaldehyde

Product 1

HCID 17747369HCID 17747369, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution (0.15 M) of 2-phenyl-1,3-thiazole-5-carbaldehyde (1.0 eq.) and CsF (0.2 eq.) in DME was treated with CF3SiMe3 (1.5 eq.) and then stiffed for 3 h at RT. The reaction mixture was quenched by adding 1N HCl and stirred for 30 min. The mixture was diluted with EtOAc, the organic phase was separated, washed with sat. aq. NaHCO3 solution and dried (Na2SO4). Evaporation of the solvent under reduced pressure afforded the product as an yellow oil. MS (ES+) C11H8F3NOS requires: 259, found: 260

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding 1N HCl
  3. additionThe mixture was diluted with EtOAc
  4. customthe organic phase was separated
  5. washwashed with sat. aq. NaHCO3 solution
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4be87b29e7e1460994d40c322ad2bcfe
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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