1-Butanol → 3-(3-Thienyl)pyridine

HRID 591381노트

반응식

HRID 591381 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[S:8]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CCC>O>[S:8]1[CH:12]=[CH:11][C:10]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:9]1

참가 물질

6

반응물 4

HCID 2631-ButanolHCID 122863-BromopyridineHCID 62657Potassium Phosphate, TribasicHCID 581760Thiophene-3-boronic acid

생성물 1

HCID 5952543-(3-Thienyl)pyridine수율 92%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

Into a glass reaction vessel equipped with a cooling apparatus were added 0.015 mmol of bis(dicyclopentyl(2-methoxyphenyl)phosphine)dichloropalladium(II), 1.5 mmol of 3-bromopyridine, 2.25 mmol of 3-thiopheneboronic acid, 3.0 mmol of potassium phosphate and 4 mL of n-butanol. The resultant mixture was stirred with heating at 100° C. for 4 hours. The resultant reaction mixture was cooled down to room temperature, 20 mL of water was added, and the mixture was extracted with 20 mL of diethyl ether twice. The resultant organic layers were mixed, and dried over anhydrous magnesium sulfate, then, filtrated, to obtain a solution. This solution was concentrated, and purified by silica gel column chromatography, to obtain 3-(3-thienyl)-pyridine with a yield of 92%.

후처리

  1. customInto a glass reaction vessel
  2. customequipped with a cooling apparatus
  3. customThe resultant reaction mixture
  4. temperaturewas cooled down to room temperature
  5. extractionthe mixture was extracted with 20 mL of diethyl ether twice
  6. additionThe resultant organic layers were mixed
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. customto obtain a solution
  10. concentrationThis solution was concentrated
  11. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1f186d8ed4054494bf2368eccc09dfbe
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238665B2

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