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

HRID 476345

反応式

HRID 476345 の反応式
[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]

参加物

5

反応物 2

HCID 57608129N,N-bis(4-methoxyphenyl)-2-oxopropanamideHCID 178491912HCID 178491912、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 18522661Acetone cardice溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-08dd2e4b9c124071be3739be5bb6b13d
出典データセット
uspto-grants-2014_01
特許番号
US08637706B2

関連ノート

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