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

HRID 487705ノート

反応式

HRID 487705 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a8b4355423aa41de975344fb5706dc8c
出典データセット
uspto-grants-1994_03
特許番号
US05296495

反応ノート

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