Ammonium Chloride → 1-(2-Methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol

HRID 892509

Reaction equation

HRID 892509 reaction equation
Br[CH:2]=[C:3]([CH3:5])[CH3:4].[Mg].[CH3:7][C:8]1[C:9]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]([C:9]1[C:8]([CH3:7])=[CH:13][CH:12]=[CH:11][N:10]=1)([OH:15])[CH:2]=[C:3]([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 985601-Bromo-2-methyl-1-propeneHCID 5462224MagnesiumHCID 198956902-(2-Methoxybenzoyl)-3-methylpyridine

Product 1

HCID 198956601-(2-Methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-olYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.23 g of 1-bromo-2-methylprop-1-ene were added dropwise to 2.5 g of magnesium turnings covered with tetrahydrofuran while heating. 7.76 g of 2-methoxyphenyl 3-methyl-2-pyridyl ketone were added while heating to reflux. After 4 hours the mixture was allowed to cool to room temperature. Saturated ammonium chloride solution was added and the resulting mixture was extracted with diethyl ether. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 5.75 g of 1-(2-methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol in the form of an oil.

Workup

  1. temperaturewhile heating
  2. temperaturewhile heating to reflux
  3. extractionthe resulting mixture was extracted with diethyl ether
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulphate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-a2126e63cfbe4f268809752ef17f8c01
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Linked notes

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