Water → HCID 21363859, compound

HRID 1348561Notes

Reaction equation

HRID 1348561 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(CC)CC)[CH:2]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][CH:14]=1.[OH-].[K+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C(OCC)(=O)C>[OH:21][CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 728512-(4-Bromophenyl)ethanolHCID 6428513-(Diethylboryl)pyridine

Product 1

HCID 21363859HCID 21363859, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 g (6.8 mmol) of (3-pyridyl)diethylborane, 0.87 ml (10.2 mmol) of 2-(4-bromophenyl)ethanol, 1.53 g (27 mmol) of KOH powder, 1.1 g (3.4 mmol) of tetrabutylammonium bromide and 0.39 g (0.34 mmol) of tetrakis(triphenylphosphine)Pd are mixed in 25 ml of anhydrous THF. The mixture is heated at reflux under a stream of argon for 4 hours. The mixture is poured into water, extraction is carried out with ethyl acetate, the organic phase is dried and the solvent is evaporated. The residue is purified by chromatography on a column of silica gel, elution being carried out with a cyclohexane/ethyl acetate=1/1 mixture, the title product thus being obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux under a stream of argon for 4 hours
  3. customthe organic phase is dried
  4. customthe solvent is evaporated
  5. customThe residue is purified by chromatography on a column of silica gel, elution

Sources & evidence

ORD record
ord-63ed20217ca24076ac20b32e47eb7ac2
Source dataset
uspto-grants-2007_05
Patent number
US07211578B2

Reaction notes

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