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

HRID 1727343ノート

反応式

HRID 1727343 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 142234762-(Benzyloxy)-4-methylpyridine収率 67%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

実験手順

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 mol) in tetrahydrofuran (50 mL) at 0° C., and the mixture was allowed to warm to room temperature and stirred for 15 minutes. To this solution was added a solution of 2-bromo-4-methylpyridine (20 mL, 110 mol) in tetrahydrofuran (50 mL), and the mixture was heated to reflux for 14 hours. Water (200 mL) was added to the reaction mixture, and extracted with ethyl acetate. The extracted solution was dried, and the solvent was distilled off. The crude product was distilled under reduced pressure to obtain a title compound (13 g, yield 67%).

後処理

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

出典と根拠

ORDレコード
ord-8cc1b29e78524b54bf418745fbe92b36
出典データセット
uspto-grants-2009_02
特許番号
US07495018B2

反応ノート

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