1-(3-Hydroxy-4-methoxyphenyl)ethanone → methyl 4-[[(E)-1-(3-hydroxy-4-methoxyphenyl)ethylideneamino]oxymethyl]benzoate

HRID 41935

反応式

HRID 41935 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[C:14]([C:18]1[CH:26]=[CH:25][C:21]([CH2:22][O:23][NH2:24])=[CH:20][CH:19]=1)([O:16][CH3:17])=[O:15]>>[C:14]([C:18]1[CH:26]=[CH:25][C:21]([CH2:22][O:23]/[N:24]=[C:10](/[C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=2)\[CH3:11])=[CH:20][CH:19]=1)([O:16][CH3:17])=[O:15]

参加物

3

反応物 2

HCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanoneHCID 18526030Methyl 4-[(aminooxy)methyl]benzenecarboxylate hydrochloride

生成物 1

HCID 25100250methyl 4-[[(E)-1-(3-hydroxy-4-methoxyphenyl)ethylideneamino]oxymethyl]benzoate収率 82%

実験手順

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(4-carbomethoxybenzyl)hydroxylamine hydrochloride (27) (72 mg, 0.331 mmol) according to the general procedure II-B defined above. After being heated at reflux for 15 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL) and the resulting solution washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The residue thus obtained was subjected to flash chromatography (1:9 v/v ethyl acetate/hexane elution) to afford the title compound CP30263 (71 mg, 82%) as a white solid, m.p. 97.7-98.7° C., Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

後処理

  1. temperatureAfter being heated
  2. temperatureat reflux for 15 h the reaction mixture
  3. temperaturewas cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe ensuing residue was dissolved in CH2Cl2 (15 mL)
  6. washthe resulting solution washed with H2O (2×10 mL)
  7. dry with materialthen dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue thus obtained
  11. washwas subjected to flash chromatography (1:9 v/v ethyl acetate/hexane elution)

出典と根拠

ORDレコード
ord-74f79918fd0142078427e8c33f1bd1af
出典データセット
uspto-grants-2013_09
特許番号
US08536157B2

関連ノート

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