Potassium Carbonate → 2-Cyclopropyloxy-5-trifluoromethoxyphenylethyne

HRID 1017258Notes

Reaction equation

HRID 1017258 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH:7]1([O:10][C:11]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][C:12]=2[CH:13]=O)[CH2:9][CH2:8]1.P(=O)(OC=[N+]=[N-])OC(=O)C>CO>[CH:7]1([O:10][C:11]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][C:12]=2[C:13]#[CH:1])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 215840762-Cyclopropoxy-5-(trifluoromethoxy)benzaldehydeHCID 178476745HCID 178476745, compound

Product 1

HCID 112765472-Cyclopropyloxy-5-trifluoromethoxyphenylethyneYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (6.15 g, 44 mmol) was added to a stirred solution of 2-cyclopropyloxy-5-trifluoromethoxybenzaldehyde (Description 3; 4.4 g, 17.8 mmol), and acetyl diazomethyl phosphonate (6.15 g, 32 mmol) in dry methanol (50 ml) at +5° C. The reaction mixture was stirred at +5° C. for 30 minutes and at room temperature for 3.5 hours. The mixture was quenched with saturated aqueous ammonium chloride and extracted into hexane (3×30 ml). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 0-45%) to give the title compound (4.2 g, 94%).

Workup

  1. customThe mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted into hexane (3×30 ml)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 0-45%)

Sources & evidence

ORD record
ord-a25e022ee3f64f0982a6406282e0053d
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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