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

HRID 2267018노트

반응식

HRID 2267018 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][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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e55d81a746c84154a753034c564e0d11
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858646B2

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