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

HRID 493214

반응식

HRID 493214 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cd34385ba4f74eed82e17c07a4fda942
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534788B2

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