Ammonium Chloride → HCID 10753521, 화합물

HRID 928882

반응식

HRID 928882 반응식
[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]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 178418918HCID 178418918, 화합물HCID 178489586HCID 178489586, 화합물

생성물 1

HCID 10753521HCID 10753521, 화합물수율 28.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-21074e248a9a4599aa5a851c4db99829
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290591B2

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