Pyridine → 3'-fluoro-4'-hydroxyacetophenone-O-4-nitrobenzyloxime

HRID 41961ノート

反応式

HRID 41961 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH3:10])[CH:5]=[CH:6][C:7]=1[OH:8].Cl.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([CH2:20][O:21][NH2:22])=[CH:18][CH:17]=1)([O-:15])=[O:14].N1C=CC=CC=1>C(O)C>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][O:21][N:22]=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([F:1])[CH:3]=2)[CH3:10])=[CH:23][CH:24]=1)([O-:15])=[O:14]

参加物

5

反応物 3

HCID 1049PyridineHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)HCID 27373251-(3-Fluoro-4-hydroxyphenyl)ethan-1-one

生成物 1

HCID 1363498393'-fluoro-4'-hydroxyacetophenone-O-4-nitrobenzyloxime

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 3′-fluoro-4′-hydroxyacetophenone (0.063 g, 0.411 mmol), O-(4-nitrobenzyl)hydroxylamine hydrochloride (0.100 g, 0.491 mmol) and pyridine (0.13 ml, 1.61 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 5h and cooled to room temperature. The solution was concentrated to a pale yellow oil which was diluted with dichloromethane/water. The resultant mixture was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to an off-white solid. The crude product was purified by column chromatography (SiO2), eluting with 8:2 petrol/ethyl acetate, to give a 3′-fluoro-4′-hydroxyacetophenone-O-4-nitrobenzyloxime (CP9-132) as light yellow solid (0.081 g, 65%),

後処理

  1. concentrationThe solution was concentrated to a pale yellow oil which
  2. additionwas diluted with dichloromethane/water
  3. extractionThe resultant mixture was extracted with dichloromethane (×3)
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to an off-white solid
  8. customThe crude product was purified by column chromatography (SiO2)
  9. washeluting with 8:2 petrol/ethyl acetate

出典と根拠

ORDレコード
ord-428838e03eb742dda3e73b743666b1ff
出典データセット
uspto-grants-2013_09
特許番号
US08536157B2

反応ノート

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