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

HRID 2212328ノート

反応式

HRID 2212328 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 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%).

後処理

  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

出典と根拠

ORDレコード
ord-d68083726e9b4b8792728e518284571f
出典データセット
uspto-grants-2006_09
特許番号
US07101899B1

反応ノート

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