Potassium Carbonate → 5-Ethynyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile

HRID 536164Notes

Reaction equation

HRID 536164 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9])=O.[N+](=[C:24](P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9])#[CH:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86666203Benzonitrile, 5-formyl-2-[3-(trifluoromethyl)phenoxy]-HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 866970245-Ethynyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-formyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile (1 g, 3.43 mmol) and dimethyl (1-diazo-2-oxopropyl)phosphonate (1.326 g, 6.87 mmol) in methanol (45 mL), was added potassium carbonate (2.373 g, 17.17 mmol) under argon. The reaction mixture was stirred for 1 h at rt, concentrated. The residue was dissolved in EtOAc (150 mL), washed with sat. ammonium hydrochloride solution (30 mL×3), water 30 mL, concentrated. Purification via ISCO system (EA/PE=1:20) afforded the title compound as a pale yellow oil. LC-MS (ESI): m/z 288 [M+H]+; 3.71 min (ret time).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc (150 mL)
  3. washwashed with sat. ammonium hydrochloride solution (30 mL×3), water 30 mL
  4. concentrationconcentrated
  5. customPurification via ISCO system (EA/PE=1:20)

Sources & evidence

ORD record
ord-86c9fb1851c745da989700b694f24279
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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