Benzyl Alcohol → 5-Benzyloxy-2-bromoisonicotinic acid ethyl ester

HRID 1516576노트

반응식

HRID 1516576 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([O:13][C:14](=[O:23])[C:15]1[C:20](F)=[CH:19][N:18]=[C:17]([Br:22])[CH:16]=1)[CH3:12].O>O1CCCC1>[CH2:11]([O:13][C:14](=[O:23])[C:15]1[C:20]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:19][N:18]=[C:17]([Br:22])[CH:16]=1)[CH3:12]

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 46311464Ethyl 2-bromo-5-fluoroisonicotinate

생성물 1

HCID 866451665-Benzyloxy-2-bromoisonicotinic acid ethyl ester수율 61.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of benzylalcohol (1.5 g) in tetrahydrofuran (30 mL) was added sodium hydride (55%, 0.3 g) under ice cooling, and this mixture was stirred at same temperature for 5 minutes. To this reaction mixture was added a solution of 2-bromo-5-fluoroisonicotinic acid ethyl ester (2.9 g) in tetrahydrofuran (30 mL), and this mixture was stirred at room temperature for 2 hours. This reaction mixture was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give the title compound (2.4 g).

후처리

  1. stirringthis mixture was stirred at room temperature for 2 hours
  2. extractionthis mixture was extracted with ethyl acetate
  3. washThis organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane)

출처 및 근거

ORD 기록
ord-d065cf9f2b0a4ff5848da959da3199fd
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227500B2

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