4-Hydroxybenzaldehyde → 4-{2-[(E)-2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzaldehyde

HRID 750947ノート

反応式

HRID 750947 の反応式
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([C:18]([F:21])([F:20])[F:19])=[O:17])=[CH:12][CH:11]=2)[O:6][CH:7]=1.[OH:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(=O)CC>[F:19][C:18]([F:21])([F:20])[S:16]([C:13]1[CH:14]=[CH:15][C:10](/[CH:9]=[CH:8]/[C:5]2[O:6][CH:7]=[C:3]([CH2:2][O:22][C:23]3[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=3)[N:4]=2)=[CH:11][CH:12]=1)=[O:17]

参加物

6

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole

生成物 1

HCID 866005604-{2-[(E)-2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzaldehyde収率 78.6%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

反応条件

温度
60 °C

実験手順

A suspension of 250 mg (0.74 mmol) 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole, 90 mg (0.74 mmol) 4-hydroxy-benzaldehyde, 147 mg (0.45 mmol) cesium carbonate and 123 mg (0.74 mmol) potassium iodide in 25 ml butanone was stirred at 60° C. over night. After evaporation, the residue was quenched with water and extracted with ethyl acetate. The extract was washed with sodium hydroxide solution and water, dried, concentrated and purified on silica. Elution with heptane/ethyl acetate 5:1 containing 1% acetic acid yielded 245 mg (78%) 4-{2-[(E)-2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzaldehyde as white crystals, melting at 144-147° C.

後処理

  1. customAfter evaporation
  2. customthe residue was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with sodium hydroxide solution and water
  5. customdried
  6. concentrationconcentrated
  7. custompurified on silica
  8. washElution with heptane/ethyl acetate 5:1 containing 1% acetic acid

出典と根拠

ORDレコード
ord-c9feb15714774a65a7ca2874a623af0b
出典データセット
uspto-grants-2008_07
特許番号
US07405231B2

反応ノート

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