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

HRID 1060016노트

반응식

HRID 1060016 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bc74aeee989445379a738542868f71b8
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521643B1

반응 노트

불러오는 중…