Methyl Thioglycolate → Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

HRID 335565

反応式

HRID 335565 の反応式
Cl[C:2]1[C:9]([C:10]#[N:11])=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[H-].[Na+].[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].[CH3:20]S(Cl)(=O)=O>C(OCC)(=O)C>[C:10]([C:9]1[CH:8]=[CH:7][C:6]2[CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[S:14][C:3]=2[CH:2]=1)#[N:11]

参加物

6

反応物 4

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 119617032-Chloro-3-cyanobenzaldehyde

生成物 1

HCID 11031280Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

2.5 g (15.1 mmol) of 2-chloro-3-cyanobenzaldehyde are reacted according to the general procedure with 0.90 g (22.7 mmol) of sodium hydride (60% pure) and 1.76 g (16.6 mmol) of methyl mercaptoacetate. The resulting reaction product is initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1) and then dissolved in 30 ml of pyridine, and 650 μl (8.4 mmol) of methanesulfonyl chloride are added. The mixture is stirred at 80° C. for 2 h. After cooling, ethyl acetate is added and the mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution, dried over sodium sulfate, concentrated and dried under high vacuum. This gives 1.63 g (49.9% of theory) of the title compound.

後処理

  1. customThe resulting reaction product
  2. customis initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1)
  3. dissolutiondissolved in 30 ml of pyridine
  4. temperatureAfter cooling
  5. washthe mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customdried under high vacuum

出典と根拠

ORDレコード
ord-cadb99b348c0446fad0682c7241d51cb
出典データセット
uspto-grants-2014_11
特許番号
US08884017B2

関連ノート

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