Triethylamine → N-(3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl)-N-methyl-2-(4-acetyl-2-isopropyl-5-methylphenoxy)ethylamine

HRID 55386ノート

反応式

HRID 55386 の反応式
[CH3:1][NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13](=[O:15])[CH3:14])=[CH:8][C:7]=1[CH:16]([CH3:18])[CH3:17].[OH:19][C:20]1[C:21]([CH3:32])=[C:22]([C:25]([O:30][CH3:31])=[C:26]([CH3:29])[C:27]=1[CH3:28])[CH2:23]Cl.C(N(CC)CC)C>CN(C)C=O>[OH:19][C:20]1[C:21]([CH3:32])=[C:22]([C:25]([O:30][CH3:31])=[C:26]([CH3:29])[C:27]=1[CH3:28])[CH2:23][N:2]([CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13](=[O:15])[CH3:14])=[CH:8][C:7]=1[CH:16]([CH3:18])[CH3:17])[CH3:1]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 109218743-Hydroxy-6-methoxy-2,4,5-trimethylbenzyl chlorideHCID 19957706N-Methyl-2-(4-acetyl-2-isopropyl-5-methylphenoxy)ethylamine

生成物 1

HCID 19957713N-(3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl)-N-methyl-2-(4-acetyl-2-isopropyl-5-methylphenoxy)ethylamine収率 95.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-Methyl-2-(4-acetyl-2-isopropyl-5-methylphenoxy)ethylamine (6.75 g) and 3-hydroxy-6-methoxy-2,4,5-trimethylbenzyl chloride (5.48 g) were dissolved in N,N-dimethylformamide (80 ml), and triethylamine (2.58 g) was added dropwise while stirring the mixture at room temperature. The mixture was stirred at room temperature for 16.5 hours. After the reaction, the solvent was distilled off, and water was added. The mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained liquid was purified by silica gel chromatography (eluent; ethyl acetate/benzene=1/1) to give 10.38 g of a pale-yellow solid. The obtained solid was recrystallized from isopropyl alcohol to give 7.22 g of the title compound (colorless crystals).

後処理

  1. stirringThe mixture was stirred at room temperature for 16.5 hours
  2. customAfter the reaction
  3. distillationthe solvent was distilled off
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe obtained organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe obtained liquid was purified by silica gel chromatography (eluent; ethyl acetate/benzene=1/1)

出典と根拠

ORDレコード
ord-c77fd0935e2f4c4cbcf3ad0c6303cb8c
出典データセット
uspto-grants-1997_04
特許番号
US05624961

反応ノート

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