Potassium Carbonate → 1233501-58-0

HRID 468855Notes

Reaction equation

HRID 468855 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-da1343eedaac4b198a7331e7d64f289c
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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