3-Pyridinecarboxaldehyde → Dipyridin-3-ylmethanol

HRID 1360116ノート

反応式

HRID 1360116 の反応式
[Li]CCCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>CCOCC>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[OH:20])[CH:8]=1

参加物

5

反応物 3

HCID 103713-PyridinecarboxaldehydeHCID 122863-BromopyridineHCID 178418339Butyllithium

生成物 1

HCID 11309949Dipyridin-3-ylmethanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

n-BuLi (42 mL, 1.6M, 67 mmol) was added to a solution of 3-bromopyridine (5.9 mL, 9.74 g, 62 mmol) in ether (200 mL) at −78 C. The resulting yellow suspension was stirred for 1 h. A solution of nicotinaldehyde (5.3 mL, 6 g, 56 mmol) in ether (25 mL) was then added. After stirring for 0.5 h, the reaction mixture was allowed to warm gradually to 0 C. The reaction mixture was then quenched by addition of half saturated brine (100 mL). The resulting mixture was extracted once with ethyl acetate and once with chloroform. Drying (1:1 Na2SO4/K2CO3) and concentration gave dipyridin-3-ylmethanol as a very viscous orange oil which was used without further purification.

後処理

  1. stirringAfter stirring for 0.5 h
  2. temperatureto warm gradually to 0 C
  3. customThe reaction mixture was then quenched by addition of half saturated brine (100 mL)
  4. extractionThe resulting mixture was extracted once with ethyl acetate and once with chloroform
  5. customDrying
  6. concentration(1:1 Na2SO4/K2CO3) and concentration

出典と根拠

ORDレコード
ord-49143ba9d6ec48de8eef3d6b31c48539
出典データセット
uspto-grants-2011_02
特許番号
US07879839B2

反応ノート

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