Potassium Carbonate → 3-Ethynylbenzonitrile

HRID 2243884Notes

Reaction equation

HRID 2243884 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[C:6]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])#[CH:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 225703183-[(Trimethylsilyl)ethynyl]benzonitrile

Product 1

HCID 120889643-EthynylbenzonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound of Example 17 (9.35 g, 47.0 mmol) and potassium carbonate (32.0 g, 235.0 mmol) was stirred in MeOH (120 mL) at RT for 15 minutes. The reaction was partitioned between water and hexanes. The organic extracts were washed with water, dried over sodium sulphate, filtered and concentrated. The reaction mixture was purified by column chromatography to afford the title product (1.45 g, 56%) as a white solid.

Workup

  1. customThe reaction was partitioned between water and hexanes
  2. washThe organic extracts were washed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe reaction mixture was purified by column chromatography

Sources & evidence

ORD record
ord-5f555f8478304a3782a4e9a079108333
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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