Benzyl Alcohol → 3-(Benzyloxy)pyridine-4-carbonitrile

HRID 2094509노트

반응식

HRID 2094509 반응식
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:19]=[N:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>CN(C=O)C>[CH2:3]([O:10][C:12]1[CH:19]=[N:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 106783063-Chloropyridine-4-carbonitrile

생성물 1

HCID 108223413-(Benzyloxy)pyridine-4-carbonitrile수율 87%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 0.59 g of 60% sodium hydride (in oil) and 5 ml of DMF was stirred while ice-cooling. To the reaction mixture, 1.59 g of benzyl alcohol was added. The reaction mixture was stirred at the same temperature for 10 minutes. To the reaction mixture, 2.0 g of 3-chloroisonicotinonitrile was added, and the reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and then to ethyl acetate was added to the reaction mixture, followed by filtration of insoluble matters. The filtrate was concentrated under reduced pressure and the resultant residue was subjected to silica gel column chromatography to give 2.64 g of 3-benzyloxy isonicotinonitrile.

후처리

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at the same temperature for 10 minutes
  3. stirringthe reaction mixture was stirred at the same temperature for 30 minutes and at room temperature for 1.5 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionto ethyl acetate was added to the reaction mixture
  6. filtrationfollowed by filtration of insoluble matters
  7. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-58a02c5a405b4b6f896b6195455d1280
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445522B2

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