N,N-bis(4-methoxyphenyl)-2-oxopropanamide → 2-hydroxy-N,N,2-tris(4-methoxyphenyl)propanamide

HRID 1694779Notes

Reaction equation

HRID 1694779 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:10](=[O:14])[C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([Mg]Br)=[CH:27][CH:26]=1>C1COCC1.C(=O)=O.CC(C)=O>[OH:13][C:11]([C:28]1[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=1)([CH3:12])[C:10]([N:9]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:14]

Participants

5

Reactant 2

HCID 57608129N,N-bis(4-methoxyphenyl)-2-oxopropanamideHCID 178491912HCID 178491912, compound

Product 1

HCID 576081272-hydroxy-N,N,2-tris(4-methoxyphenyl)propanamideYield 84.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 18522661Acetone cardiceSolvent

Conditions

Temperature
-78 °C

Procedure

N,N-bis(4-methoxyphenyl)-2-oxopropanamide (0.53 g, 1.77 mmol) was placed in a 250 mL three-necked round-bottomed flask fitted with a stirring bar, a rubber stopper and a nitrogen inlet, and dissolved in 30 mL anhydrous THF. The solution was cooled to −78° C. in dry ice-acetone bath. 4-Methoxyphenylmagnesium bromide solution (3.89 mL of 0.5 M THF solution, 7.25 mmol) was added dropwise with stirring at −78° C. under nitrogen atmosphere. The resulted solution was stirred at −78° C. for one hour and then at room temperature for one hour. The reaction was quenched by adding 20 mL of saturated NH4Cl solution. EtOAc (3×30 mL) was added to extract the solution. The organic layers were separated, washed with brine (20 mL) and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (silica gel, EtOAc/hexanes=1/1 v/v) to give a white solid product, 2-hydroxy-N,N,2-tris(4-methoxyphenyl)propanamide, 0.61 g, 84.7% yield.

Workup

  1. customfitted with a stirring bar
  2. stirringThe resulted solution was stirred at −78° C. for one hour
  3. customThe reaction was quenched
  4. additionby adding 20 mL of saturated NH4Cl solution
  5. additionEtOAc (3×30 mL) was added
  6. extractionto extract the solution
  7. customThe organic layers were separated
  8. washwashed with brine (20 mL)
  9. dry with materialdried over anhydrous MgSO4
  10. customThe solvent was removed under reduced pressure
  11. customthe residue was purified by flash column chromatography (silica gel, EtOAc/hexanes=1/1 v/v)

Sources & evidence

ORD record
ord-f50e4fafc5944807acff11b0eadb00ec
Source dataset
uspto-grants-2012_04
Patent number
US08158828B2

Reaction notes

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