Potassium Carbonate → 6-Chloro-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 493214

反応式

HRID 493214 の反応式
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][SH:21]>CS(C)=O>[CH3:24][O:23][C:19]([C:20]1[S:21][C:4]2[CH:3]=[C:2]([Cl:1])[C:9]([O:10][CH3:11])=[CH:8][C:5]=2[CH:6]=1)=[O:22]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 149282684-Chloro-2-fluoro-5-methoxybenzaldehyde

生成物 1

HCID 688807806-Chloro-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 4-chloro-2-fluoro-5-methoxybenzaldehyde (0.821 g, 4.35 mmol) in 8.7 mL of DMSO were successively added K2CO3 (1.81 g, 3 eq.) and methyl thioglycolate (0.474 mL, 1.2 eq.), and the mixture was vigorously stirred at 50° C. for 2 h. After cooling, the reaction mixture was poured onto crashed ice/HCl, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated. Flash chromatography (SiO2, hexane/AcOEt=85/15), followed by crystallization from heptane/AcOEt, yielded 0.300 g of the title compound as off-white solid.

後処理

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured
  3. extractiontwofold extracted with AcOEt
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customFlash chromatography (SiO2, hexane/AcOEt=85/15), followed by crystallization from heptane/AcOEt

出典と根拠

ORDレコード
ord-cd34385ba4f74eed82e17c07a4fda942
出典データセット
uspto-grants-2009_05
特許番号
US07534788B2

関連ノート

読み込み中…