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

HRID 1486237ノート

反応式

HRID 1486237 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=1>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 7498Benzyl BromideHCID 178428601HCID 178428601、化合物

生成物 1

HCID 142234762-(Benzyloxy)-4-methylpyridine収率 94.2%

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 13.6 ml (114 mmol, 1.0 eq.) of benzyl bromide and 15.0 g (137 mmol, 1.2 eq.) of 2-hydroxy-4-methylpyridine [CAS No: 13466-41-6] was dissolved in 470 ml of THF. The solution was admixed with 37.9 g (137 mmol, 1.2 eq.) of silver carbonate and the mixture was heated to reflux with exclusion of light overnight. Subsequently, the reaction mixture was filtered through kieselguhr and eluted with ethyl acetate, and the filtrate was concentrated. The crude product was purified by silica gel chromatography (700 g of silica gel, cyclohexane/ethyl acetate 95:5). 21.4 g of the title compound were obtained (94% of theory).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux with exclusion of light overnight
  3. filtrationSubsequently, the reaction mixture was filtered through kieselguhr
  4. washeluted with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by silica gel chromatography (700 g of silica gel, cyclohexane/ethyl acetate 95:5)

出典と根拠

ORDレコード
ord-aa12926c7dfe431ebadb71396f925803
出典データセット
uspto-grants-2016_08
特許番号
US09422285B2

反応ノート

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