Ammonium Chloride → 1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol

HRID 71153Notes

Reaction equation

HRID 71153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:25]#[C:26][CH2:27][CH2:28][CH2:29][CH:30]=[O:31])[CH:16]=[CH:17][C:18]=1[N:19]1[CH:23]=[N:22][C:21]([CH3:24])=[N:20]1.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]([OH:31])[CH2:29][CH2:28][CH2:27][C:26]#[C:25][C:15]2[CH:16]=[CH:17][C:18]([N:19]3[CH:23]=[N:22][C:21]([CH3:24])=[N:20]3)=[C:13]([O:12][CH3:11])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 866629766-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-ynalHCID 178478192HCID 178478192, compound2×

Product 1

HCID 666089951-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dichlorophenylmagnesium bromide (0.5 M THF solution, 13 mL) was added dropwise to a mixture of 6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-ynal (900 mg) in THF (32 mL) at −78° C., and the mixture was stirred for 1 hr under ice-cooling and at room temperature for 14 hr. 3,4-Dichlorophenylmagnesium bromide (0.5M THF solution, 13 mL) was added to the reaction mixture under ice-cooling, and the mixture was stirred for 1 hr under ice-cooling. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (349 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr under ice-
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fdd22228dd8b44e684b3e9880bb56cfe
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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