Carbon Dioxide → 3-Methyl-1-benzothiophene-6-carboxylic acid

HRID 280588노트

반응식

HRID 280588 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH3:10])=[CH:8][S:7][C:6]=2[CH:11]=1.CI.[Mg].[C:15](=[O:17])=[O:16]>CCOCC>[CH3:10][C:9]1[C:5]2[CH:4]=[CH:3][C:2]([C:15]([OH:17])=[O:16])=[CH:11][C:6]=2[S:7][CH:8]=1

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 13540107Benzo[b]thiophene, 6-bromo-3-methyl-

생성물 1

HCID 135401103-Methyl-1-benzothiophene-6-carboxylic acid

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A mixture of 6-bromo-3-methylbenzo[b]thiophene (16.8 g) and methyl iodide (23.8 g) was added dropwise to a stirred mixture of dry ether (150 ml) and magnesium (11.06 g) at such a rate that gentle reflux was maintained. When the addition was complete, the mixture was heated under reflux with stirring for 30 minutes, then cooled and poured onto a mixture of crushed solid carbon dioxide and ether. When all the carbon dioxide had evaporated, 2N hydrochloric acid (100 ml) was added and the mixture was shaken. The ether layer was separated and the aqueous layer was extracted with ether. The ether solutions were combined, dried (Na2SO4) and evaporated to give a solid which was crystallized from ethyl acetate to give 3-methylbenzo[b]thiophene-6-carboxylic acid (7.71 g), m.p. 230°-232° C.

후처리

  1. temperaturethat gentle reflux
  2. temperaturewas maintained
  3. additionWhen the addition
  4. temperaturethe mixture was heated
  5. temperatureunder reflux
  6. temperaturecooled
  7. customWhen all the carbon dioxide had evaporated
  8. addition2N hydrochloric acid (100 ml) was added
  9. stirringthe mixture was shaken
  10. customThe ether layer was separated
  11. extractionthe aqueous layer was extracted with ether
  12. dry with materialdried (Na2SO4)
  13. customevaporated
  14. customto give a solid which
  15. customwas crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-c845e38820a2419dbae83c7d93b09c0c
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04590200

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