Bromoethene → 1-(4-Chlorophenyl)-1-(3-pyridyl)-2-propen-1-ol

HRID 1649539Notes

Reaction equation

HRID 1649539 reaction equation
[CH:1](Br)=[CH2:2].[Mg].[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:8][CH:7]=1.[Cl-].[NH4+]>O1CCCC1.O>[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)([OH:11])[CH:1]=[CH2:2])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 11641BromoetheneHCID 25517Ammonium ChlorideHCID 845184-Chlorophenyl pyridin-3-yl ketoneHCID 5462224Magnesium

Product 1

HCID 127170981-(4-Chlorophenyl)-1-(3-pyridyl)-2-propen-1-olYield 119.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of vinylbromide (11.8 g, 110 mmol) in 40 ml tetrahydrofuran was added to a mixture of magnesium (2.79 g, 115 mmol) in 20 ml tetrahydrofuran under a nitrogen atmosphere at 50° to 60° C. After reflux for 1 h 3-(4-chlorobenzoyl)pyridine (21.8 g, 0.100 mol) in 100 ml tetrahydrofuran was added at 10° C. After stirring for 1 h a solution of 8 g ammonium chloride in 40 ml water was added and the mixture filtrated. The organic phase was dried over sodium sulphate and evaporated to give 29.4 g of a red oil containing 20% unreacted starting ketone. This crude product was used directly in the next step (Example C).

Workup

  1. additionwas added at 10° C
  2. additionwas added
  3. filtrationthe mixture filtrated
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-b7eb528873d74d20821d6db36802c3f3
Source dataset
uspto-grants-1983_11
Patent number
US04418065

Reaction notes

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