1-(3-Hydroxy-4-methoxyphenyl)ethanone → 5-[(E)-N-[(2-fluorophenyl)methoxy]-C-methylcarbonimidoyl]-2-methoxyphenol

HRID 41938

反応式

HRID 41938 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.[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][O:18][NH2:19]>C(OCC)(=O)C.CCCCCC>[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][O:18]/[N:19]=[C:10](/[C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=1)\[CH3:11]

参加物

4

反応物 2

HCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanoneHCID 21192890O-(2-Fluorobenzyl)hydroxylamine hydrochloride

生成物 1

HCID 251004085-[(E)-N-[(2-fluorophenyl)methoxy]-C-methylcarbonimidoyl]-2-methoxyphenol収率 91%

試薬・触媒・溶媒 1

HCID 21226206Ethyl acetate hexane溶媒2 回

実験手順

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(2-fluorobenzyl)hydroxylamine hydrochloride (32) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 36 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 oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane) to afford the title compound CP30280 (79 mg, 91%) as a pale-yellow oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

後処理

  1. temperatureAfter being heated for 36 h the reaction mixture
  2. temperaturewas cooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe ensuing residue was dissolved in CH2Cl2 (15 mL)
  5. washthe resulting solution washed with H2O (2×10 mL)
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe oil thus obtained

出典と根拠

ORDレコード
ord-a1cb47cc8f73450e8f575565cb87c1e6
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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