Hydroxyamine hydrochloride → 1-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-3-yl]-ethanone oxime

HRID 1836035노트

반응식

HRID 1836035 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[C:7]([C:17](=O)[CH3:18])[C:6]=2[CH:20]=1.[NH2:21][OH:22].Cl>CCO.N1C(=O)CC[C@H]1C(O)=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[C:7]([C:17](=[N:21][OH:22])[CH3:18])[C:6]=2[CH:20]=1

참가 물질

4

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 222216281-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-3-yl]-ethanone

생성물 1

HCID 1371789481-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-3-yl]-ethanone oxime수율 6.5%

시약·촉매·용매 1

HCID 131724523EtOH Pyr용매

실험 절차

Ketone 110 (1.9 g, 7.1 mmol) was dissolved in a solution of EtOH/Pyr (50 mL/10 mL) and treated with NH2OH—HCl (0.5 g, 7.2 mmol) and heated at reflux until all of the starting material was consumed by TLC analysis. The reaction was worked up by concentrating down and partitioning the residue between EtOAc and 2 N HCl aq, washing the EtOAc layer with saturated NaHCO3 aq, brine and drying over MgSO4. The solution was then filtered, concentrated and chromatographed on silica gel (1:4 EtOAc/hexanes) and the product obtained triturated with CH2Cl2 to yield 0.131 g of the pure oxime. Stereochemistry of the oxime was tentatively defined as cis since no NOE effect between the oxime hydroxyl proton and the adjacent methyl group could be observed: Mp=217° C.; 1H NMR (DMSO-d6) δ 11.27 (s, 1 H), 9.94 (br s, 1 H), 9.23 (br s, 1 H), 7.51 (d, 2 H, J=8.8 Hz), 7.36 (d, 1 H, J=8.3 Hz), 7.03 (d, 1 H, J=2.4 Hz), 6.88 (d, 2 H, J=8.8 Hz), 6.74 (dd, 1 H, J=8.8 Hz, 2.4 Hz), 1.99 (s, 3 H).

후처리

  1. temperatureheated
  2. temperatureat reflux until all of the starting material
  3. customwas consumed by TLC analysis
  4. concentrationby concentrating down
  5. custompartitioning the residue between EtOAc and 2 N HCl aq
  6. washwashing the EtOAc layer with saturated NaHCO3 aq, brine
  7. dry with materialdrying over MgSO4
  8. filtrationThe solution was then filtered
  9. concentrationconcentrated
  10. customchromatographed on silica gel (1:4 EtOAc/hexanes)
  11. customthe product obtained
  12. customtriturated with CH2Cl2

출처 및 근거

ORD 기록
ord-33b1be52442d4f02a164479279c9d5d1
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774248B2

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