3-Pyridinecarboxaldehyde → Dipyridin-3-ylmethanol

HRID 1360116노트

반응식

HRID 1360116 반응식
[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

참가 물질

5

반응물 3

HCID 103713-PyridinecarboxaldehydeHCID 122863-BromopyridineHCID 178418339Butyllithium

생성물 1

HCID 11309949Dipyridin-3-ylmethanol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-49143ba9d6ec48de8eef3d6b31c48539
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879839B2

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