Potassium Carbonate → 5-(4-Fluorophenyl)-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

HRID 1516693Notes

Reaction equation

HRID 1516693 reaction equation
FC(F)(F)S(O[C:7]1[C:16]([CH:17]=[O:18])=[C:15]([CH:19]([CH3:21])[CH3:20])[CH:14]=[C:13]2[C:8]=1[C:9](=[O:24])[CH2:10][C:11]([CH3:23])([CH3:22])[O:12]2)(=O)=O.[F:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:7]2[C:16]([CH:17]=[O:18])=[C:15]([CH:19]([CH3:20])[CH3:21])[CH:14]=[C:13]3[C:8]=2[C:9](=[O:24])[CH2:10][C:11]([CH3:22])([CH3:23])[O:12]3)=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2856454-Fluorophenylboronic acidHCID 580029926-Formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate

Product 1

HCID 580030235-(4-Fluorophenyl)-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 800 mg (2.03 mmol) of 6-formyl-7-isopropyl-2,2-dimethyl-4-oxo-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (Example 19A), 369 mg (2.64 mmol) of 4-fluorophenyl-boronic acid, 164 mg (142 μmol) of tetrakis(triphenylphosphine)palladium and 731 mg (3.45 mmol) of potassium carbonate and 10 ml of degassed dioxane is stirred at 100° C. overnight. After cooling to room temperature, ammonium chloride solution is added and the mixture is extracted twice with ethyl acetate. After drying of the combined organic phases over sodium sulfate, the solvent is removed under reduced pressure and the residue is purified by column chromatography (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 20:1).

Workup

  1. extractionthe mixture is extracted twice with ethyl acetate
  2. dry with materialAfter drying of the combined organic phases over sodium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customthe residue is purified by column chromatography (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-9a2438e669ef40e7979068b8b894861a
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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