Benzyl Alcohol → 2-(Benzyloxy)-4-methylpyridine

HRID 1178570노트

반응식

HRID 1178570 반응식
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1.O>CCCCCC.O1CCCC1>[C:4]1([CH2:3][O:10][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 27340872-Bromo-4-methylpyridine

생성물 1

HCID 142234762-(Benzyloxy)-4-methylpyridine수율 67%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

Sodium hydride (60% paraffin dispersion, 5.0 g, 120 mmol) was washed with hexane (5 mL) twice and suspended in tetrahydrofuran (200 mL). To this suspension was added dropwise a solution of benzyl alcohol (14 g, 120 mmol) in tetrahydrofuran (50 mL) at 0° C. and then, the mixture was allowed to warm up to room temperature with stirring for 15 minutes. To this solution was added a solution of 2-bromo-4-methylpyridine (19.5 mL, 110 mmol) in tetrahydrofuran (50 mL) and heated to reflux for 14 hours. To the reaction mixture was added water (200 mL) and extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The crude product was distilled under reduced pressure to obtain 13 g of the title compound (67 mmol, yield 67%).

후처리

  1. temperatureheated
  2. temperatureto reflux for 14 hours
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. distillationthe solvent was distilled off
  6. distillationThe crude product was distilled under reduced pressure

출처 및 근거

ORD 기록
ord-3026027910d644829784d3b5f40ad09f
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276527B2

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