1-Butanol → 3-(3-Thienyl)pyridine

HRID 591381ノート

反応式

HRID 591381 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 5952543-(3-Thienyl)pyridine収率 92%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-1f186d8ed4054494bf2368eccc09dfbe
出典データセット
uspto-grants-2016_01
特許番号
US09238665B2

反応ノート

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