Ammonium Chloride → N-{5-[2-(4-{5-[hydroxy(4-methylphenyl)methyl]-2-thienyl}phenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide

HRID 1641571Notes

Reaction equation

HRID 1641571 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]3([NH:24][C:25](=[O:27])[CH3:26])[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=[O:2].[C:28]1([CH3:36])[CH:33]=[CH:32][C:31]([Mg]Br)=[CH:30][CH:29]=1.[Cl-].[NH4+]>O1CCCC1>[OH:2][CH:1]([C:31]1[CH:32]=[CH:33][C:28]([CH3:36])=[CH:29][CH:30]=1)[C:3]1[S:7][C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]3([NH:24][C:25](=[O:27])[CH3:26])[CH2:17][O:18][C:19]([CH3:22])([CH3:23])[O:20][CH2:21]3)=[CH:12][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 57624621N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamideHCID 178418370HCID 178418370, compound

Product 1

HCID 57624590N-{5-[2-(4-{5-[hydroxy(4-methylphenyl)methyl]-2-thienyl}phenyl)ethyl]-2,2-dimethyl-1,3-dioxan-5-yl}acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(5-{2-[4-(5-formyl-2-thienyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamide (0.25 g) in tetrahydrofuran (20 mL) was added dropwise a solution (1 mol/L, 1.36 mL) of p-tolylmagnesium bromide in tetrahydrofuran at 0° C. under a nitrogen atmosphere, and the mixture was stirred at the same temperature for 1 hr. 0.5M Aqueous ammonium chloride solution (30 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.35 g) as a brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9260193de1240efa9c79a8b73065e86
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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