Water → 3-[3-[2-(4-Bromophenyl)-5,5-dimethyl-1,3-dioxane-2-yl]propoxy]benzonitrile

HRID 747711Notes

Reaction equation

HRID 747711 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([CH2:27][CH2:28][CH2:29]Cl)[O:24][CH2:23][C:22]([CH3:26])([CH3:25])[CH2:21][O:20]2)=[CH:15][CH:14]=1.O>CN(C)C=O>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2([CH2:27][CH2:28][CH2:29][O:3][C:4]3[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=3)[C:7]#[N:8])[O:20][CH2:21][C:22]([CH3:25])([CH3:26])[CH2:23][O:24]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 133943-CyanophenolHCID 24758Sodium hydrideHCID 126147752-(4-Bromophenyl)-2-(3-chloropropyl)-5,5-dimethyl-1,3-dioxane

Product 1

HCID 688339843-[3-[2-(4-Bromophenyl)-5,5-dimethyl-1,3-dioxane-2-yl]propoxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

236 mg (5.9 mmol) of sodium hydride (oily, 60%) was stirred in dimethylformamide. 691 mg (5.8 mmol) of 3-hydroxybenzonitrile was added thereto under cooling with ice. After stirring at room temperature for 30 minutes, a solution of 2 g (5.75 mmol) of 2-(4-bromophenyl)-2-(3-chloropropyl)-5,5-dimethyl-1,3-dioxane in dimethylformamide was added to the reaction mixture, and they were stirred at 100° C. overnight. Water was added to the mixture. After the extraction with ethyl acetate, the organic layer was washed with 1 N aqueous sodium hydroxide solution and saturated aqueous common salt solution and dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain the crude title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringwere stirred at 100° C. overnight
  3. extractionAfter the extraction with ethyl acetate
  4. washthe organic layer was washed with 1 N aqueous sodium hydroxide solution and saturated aqueous common salt solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c89b107a172a4c6680b496a1efeacb7b
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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