Water → HCID 178444526, compound

HRID 2099003Notes

Reaction equation

HRID 2099003 reaction equation
[Cl:1][C:2]1[C:3]([F:18])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1O.[C:19](=[O:22])([O-])[O-].[K+].[K+].O.[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[Cl:1][C:2]1[C:3]([F:18])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[O:22][CH2:19][C@H:29]1[CH2:30][CH2:31][C@H:26]([CH2:32][CH2:3][CH2:2][CH2:7][CH3:6])[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 11430Potassium CarbonateHCID 57793288HCID 57793288, compound

Product 1

HCID 178444526HCID 178444526, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4.0 g of the compound (b67) obtained in the second step was dissolved in 20 mL of N,N,-dimethylformamide. After suspending 2.5 g of potassium carbonate in the solution, 5.6 g of the compound (b68) was added thereto, followed by stirring for 6 hours at 70° C. After completing the reaction, water and toluene were added to the reaction mixture, followed by mixing. Thereafter, the mixture was left at rest to separate into an organic layer and an aqueous layer, followed by extracting to the organic layer. The resulting organic layer was washed sequentially with water, a 2N sodium hydroxide aqueous solution, a saturated sodium chloride aqueous solution and water, and then concentrated under reduced pressure to obtain a residue. 7.7 g of the residue was purified by a preparative column chromatography using a mixed solvent of heptane and toluene (heptane/toluene=3/1 by volume) as a developing solvent and silica gel as a mediator, and further purified by repeating recrystallization from a mixed solvent of heptane and Solmix A-11 (heptane/Solmix A-11=2/1 by volume) to obtain 3-chloro-2-fluoro-4-(trans-4-pentyl-cyclohexylmethoxy)-4′-propylbiphenyl (C264) as colorless crystals. The yield was 89.5% based on the compound (b67).

Workup

  1. additionwas added
  2. additionwere added to the reaction mixture
  3. additionby mixing
  4. waitThereafter, the mixture was left at rest
  5. customto separate into an organic layer
  6. extractionby extracting to the organic layer
  7. washThe resulting organic layer was washed sequentially with water
  8. concentrationa 2N sodium hydroxide aqueous solution, a saturated sodium chloride aqueous solution and water, and then concentrated under reduced pressure
  9. customto obtain a residue
  10. custom7.7 g of the residue was purified by a preparative column chromatography
  11. customfurther purified
  12. customrecrystallization from a mixed solvent of heptane and Solmix A-11 (heptane/Solmix A-11=2/1 by volume)

Sources & evidence

ORD record
ord-4e71eed955f54c15ba4320e5dace38ea
Source dataset
uspto-grants-2009_08
Patent number
US07569258B2

Reaction notes

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