1-[2-Hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone → 1-{4-[(3-Aminophenyl)methoxy]-2-hydroxy-3-propylphenyl}ethan-1-one

HRID 2244032ノート

反応式

HRID 2244032 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][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:22](=[O:24])[CH3:23]>C(O)(=O)C.ClCCl.[Zn]>[NH2:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][O:11][C:6]1[CH:5]=[CH:4][C:3]([C:22](=[O:24])[CH3:23])=[C:2]([OH:1])[C:7]=1[CH2:8][CH2:9][CH3:10]

参加物

5

反応物 1

HCID 684320061-[2-Hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone

生成物 1

HCID 145235601-{4-[(3-Aminophenyl)methoxy]-2-hydroxy-3-propylphenyl}ethan-1-one収率 536.6%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

Add zinc (21.6 g, 331 mmol) slowly to a solution of 1-[2-hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone (10.9 g, 6.07 mmol) in glacial acetic acid (120 mL). Stir the mixture for 3 hours. Dilute with dichloromethane (600 mL). Filter the reaction mixture through celite. Wash the celite pad several times with dichloromethane. Concentrate the combined filtrates. Partition the residue between ethyl acetate and saturated sodium bicarbonate. Wash the organic layer with brine, dry and concentrate to afford the title compound as a yellow solid (9.75 g, 98%): 1H NMR (CDCl3) δ 0.96 (t, 3H), 1.58 (sextet, 2H), 2.54 (s, 3H), 2.71 (t, 2H), 5.07 (s, 2H), 6.46 (d, 1H), 6.62 (d, 1H), 6.71 (s, 1H), 6.78 (d, 1H), 7.16 (t, 1H), 7.54 (d, 1H), 12.75 (s, 1H).

後処理

  1. filtrationFilter the reaction mixture through celite
  2. washWash the celite pad several times with dichloromethane
  3. concentrationConcentrate the combined filtrates
  4. customPartition the residue between ethyl acetate and saturated sodium bicarbonate
  5. washWash the organic layer with brine
  6. customdry
  7. concentrationconcentrate

出典と根拠

ORDレコード
ord-df4e5a22b1a74b6cb739268ee461a985
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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