Hydrochloric Acid → 1-[4-(4-Amino-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone

HRID 2244012ノート

反応式

HRID 2244012 の反応式
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:22](=[O:24])[CH3:23].Cl>O1CCCC1>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:11][C:6]2[CH:5]=[CH:4][C:3]([C:22](=[O:24])[CH3:23])=[C:2]([OH:1])[C:7]=2[CH2:8][CH2:9][CH3:10])=[CH:14][CH:15]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 684304651-[2-Hydroxy-4-(4-nitro-benzyloxy)-3-propyl-phenyl]-ethanone

生成物 1

HCID 684314821-[4-(4-Amino-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 1-[2-hydroxy-4-(4-nitro-benzyloxy)-3-propyl-phenyl]-ethanone (1.0 g, 3.0 mmol) in tetrahydrofuran (13 mL) is added concentrated hydrochloric acid (2.7 mL) and stannous chloride dihydrate (2.2 g, 9.9 mmol). The reaction mixture is stirred at room temperature overnight. The reaction mixture is quenched into saturated aqueous NH4Cl (100 mL). The resulting emulsion is filtered and the filtrate extracted with ethyl acetate (3×100 mL). The combined organic layers are washed with brine, dried over sodium sulfatesodium sulfate, and concentrated to provide the title compound in crude form (980 mg,). LC-MS (m/z): 298 (M−1).

後処理

  1. customThe reaction mixture is quenched into saturated aqueous NH4Cl (100 mL)
  2. filtrationThe resulting emulsion is filtered
  3. extractionthe filtrate extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulfatesodium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-f957160f11c44987b6bade30b808187d
出典データセット
uspto-grants-2010_03
特許番号
US07678794B2

反応ノート

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