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

HRID 476345

Reaction equation

HRID 476345 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 stiffing 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 stiffing 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 stiffing bar
  2. customwith stiffing at −78° C. under nitrogen atmosphere
  3. waitat room temperature for one hour
  4. customThe reaction was quenched
  5. additionby adding 20 mL of saturated NH4Cl solution
  6. additionEtOAc (3×30 mL) was added
  7. extractionto extract the solution
  8. customThe organic layers were separated
  9. washwashed with brine (20 mL)
  10. dry with materialdried over anhydrous MgSO4
  11. customThe solvent was removed under reduced pressure
  12. customthe residue was purified by flash column chromatography (silica gel, EtOAc/hexanes=1/1 v/v)

Sources & evidence

ORD record
ord-08dd2e4b9c124071be3739be5bb6b13d
Source dataset
uspto-grants-2014_01
Patent number
US08637706B2

Linked notes

Loading…