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

HRID 1694779

反応式

HRID 1694779 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 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.

後処理

  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)

出典と根拠

ORDレコード
ord-f50e4fafc5944807acff11b0eadb00ec
出典データセット
uspto-grants-2012_04
特許番号
US08158828B2

関連ノート

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