Potassium Carbonate → 1233501-58-0

HRID 1502372Notes

Reaction equation

HRID 1502372 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]#[C:10][Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]#[CH:10]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 71115286HCID 71115286, compound

Product 1

HCID 509987931233501-58-0

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of ((2-chloro-5-fluorophenyl)ethynyl)trimethylsilane (4.2 g, 18 mmol) in methanol (40 mL) was added potassium carbonate (7.7 g, 56 mmol), and the reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was then diluted with diethyl ether (100 mL) and washed with water (300 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 220 g, ISCO, heptane) to afford the title compound as a pale yellow, waxy solid (2.0 g, 70%), which was used in the next step without further purification.

Workup

  1. washwashed with water (300 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a residue that
  7. customwas purified by flash chromatography (silica, 220 g, ISCO, heptane)

Sources & evidence

ORD record
ord-3fa489fd7e4e40bf81eb6c464c6c2a63
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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