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

HRID 2267029노트

반응식

HRID 2267029 반응식
[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]

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2cba0cf60e604add8a0f1f9d8d2dd463
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858646B2

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