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

HRID 2267018ノート

反応式

HRID 2267018 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-e55d81a746c84154a753034c564e0d11
出典データセット
uspto-grants-2010_12
特許番号
US07858646B2

反応ノート

読み込み中…