Formamide → 5-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester

HRID 1914593

反応式

HRID 1914593 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=O)[CH2:11]Br)[S:7][CH:6]=1)=[O:4].S(=O)(=O)(O)O.[CH:19]([NH2:21])=[O:20]>>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[N:21]=[CH:19][O:20][CH:11]=2)[S:7][CH:6]=1)=[O:4]

参加物

4

反応物 3

HCID 713FormamideHCID 1118Sulfuric AcidHCID 539045465-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester

生成物 1

HCID 581102445-Oxazol-4-yl-thiophene-3-carboxylic acid methyl ester

反応条件

温度
150 °C

実験手順

5-(2-Bromo-acetyl)-thiophene-3-carboxylic acid methyl ester (0.60 g, 2.28 mmol) was suspended in formamide (10 mL) then sulfuric acid (1 mL) was added and the tube purged with nitrogen then sealed. The mixture was heated at 150° C. by microwave irradiation for 15 minutes. The resultant solution was diluted with HCl (1 N) and water and extracted with ethyl acetate (×3). The organic phase was dried over sodium sulfate and evaporated then purified by chromatography on a silica II cartridge, eluting with 1:1 DCM:cyclohexane to afford 5-oxazol-4-yl-thiophene-3-carboxylic acid methyl ester as a pale yellow solid (0.197 g). LCMS m/z 210.14 [M+H]+ R. T.=3.64 min (Analytical Method 9).

後処理

  1. customthe tube purged with nitrogen
  2. customthen sealed
  3. additionThe resultant solution was diluted with HCl (1 N) and water
  4. extractionextracted with ethyl acetate (×3)
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated
  7. customthen purified by chromatography on a silica II cartridge
  8. washeluting with 1:1 DCM

出典と根拠

ORDレコード
ord-81f9109593554d81b4f5f8e543e1fb83
出典データセット
uspto-grants-2013_12
特許番号
US08614209B2

関連ノート

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