Potassium Fluoride → HCID 57558493, compound

HRID 1724005Notes

Reaction equation

HRID 1724005 reaction equation
[CH3:1][C:2]1([CH3:38])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12](=[O:37])[CH:13](OS(C3C=CC(C)=CC=3)(=O)=O)[C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[CH:8]=2)[O:3]1.[F-:39].[K+]>C(#N)C.O>[CH3:1][C:2]1([CH3:38])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12](=[O:37])[CH:13]([F:39])[C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[CH:8]=2)[O:3]1

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 57436873HCID 57436873, compound

Product 1

HCID 57558493HCID 57558493, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of toluene-4-sulfonic acid 2-(2,2-dimethyl-chroman-6-yl)-2-oxo-1-(3,4,5-trimethoxy-phenyl)-ethyl ester (21.6 mg, 0.04 mmol) in anhydrous ACN (0.5 mL) is added KF (4.72 mg, 0.08 mmol) and Kryptofix (30.6 mg, 0.08 mmol). After completion of addition the reaction mixture is heated to 90° C. After 15 minutes, the reaction mixture is cooled down to room temperature and diluted with water. The aqueous layer is separated and extracted with ethyl acetate (3×). All combined organic layers are dried over Na2SO4, filtered, and concentrated to yield an oil. The crude material is purified using reverse phase to yield the desired compound.

Workup

  1. additionAfter completion of addition the reaction mixture
  2. temperaturethe reaction mixture is cooled down to room temperature
  3. customThe aqueous layer is separated
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialAll combined organic layers are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield an oil
  9. customThe crude material is purified

Sources & evidence

ORD record
ord-beb7f155c73448daa34c78ce4443dae0
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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