Sodium Iodide → 4-Tert-butyl-2-[5-(2-formylphenylmethoxy)benzofuran-2-yl]thiazole

HRID 487705노트

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HRID 487705 반응식
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27]Cl)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[I-].[Na+].C(=O)([O-])[O-:32].[Na+].[Na+]>CS(C)=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH:27]=[O:32])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 190928204-Tert-butyl-2-[5-(2-chloromethylphenylmethoxy)benzofuran-2-yl]thiazole

생성물 1

HCID 190926964-Tert-butyl-2-[5-(2-formylphenylmethoxy)benzofuran-2-yl]thiazole수율 50.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
100 °C

실험 절차

A mixture of 4-tert-butyl-2-[5-(2-chloromethylphenylmethoxy)benzofuran-2-yl]thiazole (1.56 g), sodium iodide (0.50 g) and sodium carbonate (0.83 g) in dimethylsulfoxide (15 ml) was stirred at 100° C. for 10 hours. After being cooled, the resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and toluene (1:20). The fractions containing object compound were combined and concentrates under reduced pressure to give 4-tert-butyl-2-[5-(2-formylphenylmethoxy)benzofuran-2-yl]thiazole (0.75 g).

후처리

  1. temperatureAfter being cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with a mixture of ethyl acetate and toluene (1:20)
  7. additionThe fractions containing object compound

출처 및 근거

ORD 기록
ord-a8b4355423aa41de975344fb5706dc8c
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05296495

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