Ethanol → 3-(Benzyloxy)-4-(2-methoxyethoxy)aniline

HRID 1482680ノート

反応式

HRID 1482680 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[O:18][CH2:19][CH2:20][O:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>O.CCCCCC.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=1[O:18][CH2:19][CH2:20][O:21][CH3:22])[NH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 702EthanolHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 867243352-(Benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene

生成物 1

HCID 867243363-(Benzyloxy)-4-(2-methoxyethoxy)aniline収率 33.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
80 °C

実験手順

In a 50 mL 3-neck RBF equipped with a magnetic stirrer, reflux condenser, and thermo pocket were charged 2-(benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene (2.00 g), ethanol (15 mL) and SnCl2 (4.49 g). The reaction mixture was heated to 80° C. for 3 hr. The reaction was monitored by TLC using hexane:ethyl acetate (5:5) as mobile phase. After completion, the reaction mixture was allowed to cool at room temperature. The reaction mixture was poured in water and basified by using saturated sodium bicarbonate solution. Product was extracted with ethyl acetate (50 mL×3) and the organic layer was washed with 50 mL brine solution. Organic layer was dried over sodium sulfate and concentrated under reduced pressure. Crude material was purified by using Combiflash chromatography. Product was eluted with 30% ethyl acetate in hexane to give 0.600 g of 3-(benzyloxy)-4-(2-methoxyethoxy)aniline. 1H NMR: DMSO-d6 (400 MHz): 3.348 (s, 3H), 3.556-3.580 (t, 2H, J=4.8), 3.928-3.951 (t, 2H, J=4.4), 4.702 (s, 2H), 5.006 (s, 2H), 6.004-6.031 (dd, 1H, J=2.4, 6), 6.334-6.340 (d, 1H, J=2.4), 6.676-6.697 (d, 1H, J=8.4), 7.303-7.339 (m, 1H), 7.373-7.410 (m, 2H), 7.438-7.747 (m, 2H).

後処理

  1. customIn a 50 mL 3-neck RBF equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureto cool at room temperature
  4. extractionProduct was extracted with ethyl acetate (50 mL×3)
  5. washthe organic layer was washed with 50 mL brine solution
  6. dry with materialOrganic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customCrude material was purified
  9. washProduct was eluted with 30% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-37a57ea0b459416f92cf34f7605848a2
出典データセット
uspto-grants-2016_08
特許番号
US09415049B2

反応ノート

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