Ammonium Chloride → HCID 10753521、化合物

HRID 928882

反応式

HRID 928882 の反応式
[CH:1](=[N:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([Mg]Cl)([CH3:19])[CH3:18].[NH4+].[Cl-]>C1COCC1>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:17]([CH3:19])[CH3:18]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 178418918HCID 178418918、化合物HCID 178489586HCID 178489586、化合物

生成物 1

HCID 10753521HCID 10753521、化合物収率 28.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To (E)-N-benzylidene-2-methoxyaniline (5.00 g, 23.7 mmol, 1.00 equiv) in anhydrous THF (106 mL) at 0° C. was added isopropylmagnesium chloride (13.0 mL, 2.0 M in Et2O, 26.0 mmol, 1.10 equiv) and the reaction mixture was stirred at 0° C. for 1 h. A saturated aqueous solution of NH4Cl (50 mL) was added and the aqueous layer was extracted with Et2O (3×50 mL). The combined organic layers were washed with brine (25 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography on SiO2, eluting with 2% v/v EtOAc/hexanes, to give 2-methoxy-N-(2-methyl-1-phenylpropyl)aniline as a colorless oil (1.72 g, 28% yield).

後処理

  1. extractionthe aqueous layer was extracted with Et2O (3×50 mL)
  2. washThe combined organic layers were washed with brine (25 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on SiO2
  7. washeluting with 2% v/v EtOAc/hexanes

出典と根拠

ORDレコード
ord-21074e248a9a4599aa5a851c4db99829
出典データセット
uspto-grants-2016_03
特許番号
US09290591B2

関連ノート

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