Potassium Carbonate → 1-Ethynyl-3-(trifluoromethyl)benzene

HRID 59335

Reaction equation

HRID 59335 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=1)#[CH:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 42818851-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzene

Product 1

HCID 27784901-Ethynyl-3-(trifluoromethyl)benzeneYield 142.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trimethyl((3-(trifluoromethyl)phenyl)ethynyl)silane (0.500 g, 2.06 mmol) in ethanol (10 mL) was added potassium carbonate (0.253 g, 1.8 mmol) and the reaction mixture was stirred at RT for 18 h. The reaction mass was quenched in water, neutralized with dil. HCl and extracted with hexane and concentrated to afford 0.200 g of the crude product which was further purified by column chromatography using silica (60-120 mesh) eluting with pet. ether to afford 0.500 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 4.41 (s, 1H), 7.64 (d, J=7.5 Hz, 1H), 7.77-7.81 (m, 3H).

Workup

  1. customThe reaction mass was quenched in water
  2. extractionextracted with hexane
  3. concentrationconcentrated
  4. customto afford 0.200 g of the crude product which
  5. customwas further purified by column chromatography
  6. washeluting with pet. ether

Sources & evidence

ORD record
ord-c30f806652554078a63ae90949880c26
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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