Potassium Hydroxide → HCID 22718333, compound

HRID 1582765Notes

Reaction equation

HRID 1582765 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.C(B(CC)[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)C.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:2]2[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=2)[CH:16]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 991682-(p-Bromophenoxy)ethanolHCID 6428513-(Diethylboryl)pyridine

Product 1

HCID 22718333HCID 22718333, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a nitrogen atmosphere, 2-(4-bromophenoxy)ethanol 500 mg, diethyl (3-pyridyl) borane 509 mg, finely pulverized potassium hydroxide 388 mg, tetra-n-butyl ammonium bromide 74 mg and a tetrakis-triphenyl phosphine palladium complex 133 mg were added to tetrahydrofuran 10 ml and stirred under reflux with heating. After stirring for 2 hours, the mixture was cooled to room temperature and partitioned by adding water and ethyl acetate. The organic layer was washed with water and then with brine, dried over magnesium sulfate anhydride, and evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound (233 mg, 50%) was obtained as a pale yellow crystalline.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. stirringAfter stirring for 2 hours
  4. custompartitioned
  5. additionby adding water and ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialwith brine, dried over magnesium sulfate anhydride
  8. customevaporated
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound (233 mg, 50%)
  10. customwas obtained as a pale yellow crystalline

Sources & evidence

ORD record
ord-88339ca383304906ba580872e0390ba0
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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