Sodium Hydroxide → 2-(4-(4-Methylpyridin-2-yl)-2-nitrophenyl)-1,3-dioxolane

HRID 1060016ノート

反応式

HRID 1060016 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=2)[CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].[OH2:25].[C:26]1([CH3:36])C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)CO>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]3[O:25][CH2:26][CH2:36][O:13]3)=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=2)[CH:3]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 521998p-Toluenesulfonic acid monohydrateHCID 186675944-(4-Methylpyridin-2-yl)-2-nitrobenzaldehyde

生成物 1

HCID 186674852-(4-(4-Methylpyridin-2-yl)-2-nitrophenyl)-1,3-dioxolane収率 75.2%

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 1140Toluene溶媒

実験手順

To a suspension of 4-(4-methylpyridin-2-yl)-2-nitrobenzaldehyde (242 mg), ethyleneglycol (1.2 ml) and magnesium sulfate (1.0 g) in toluene (5 ml) was added p-toluenesulfonic acid monohydrate (209 mg), and the resultant suspension was refluxed for 5 hours. After cooling, the mixture was poured into 0.1N aqueous sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, 25% ethyl acetate in n-hexane) to give 2-(4-(4-methylpyridin-2-yl)-2-nitrophenyl)-1,3-dioxolane (215 mg).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 25 g, 25% ethyl acetate in n-hexane)

出典と根拠

ORDレコード
ord-bc74aeee989445379a738542868f71b8
出典データセット
uspto-grants-2003_02
特許番号
US06521643B1

反応ノート

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