Benzyl Bromide → 3-(benzyloxy)-5-bromopyridin-2(1H)-one

HRID 625931ノート

反応式

HRID 625931 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5](=[O:8])[NH:6][CH:7]=1.[OH-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:12]([O:9][C:4]1[C:5](=[O:8])[NH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 125630835-Bromopyridine-2,3-diol

生成物 1

HCID 674068463-(benzyloxy)-5-bromopyridin-2(1H)-one収率 38.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4.4 g (23.2 mmol) 5-bromo-3-hydroxy-1H-pyridin-2-one and 1.2 g (30 mmol) NaOH in 116 mL MeOH was added benzyl bromide dropwise at room temperature. The resulting mixture was heated to 60° C. overnight. After cooling, the volatiles were removed in vacuo, 20 mL water and 40 mL EtOAc were added, and the aqueous phase was extracted 2× with 20 mL EtOAc. The combined organics were dried over Na2SO4 and evaporated. Purification by automated flash chromatography (80 g silica gel cartridge 0-100% EtAOc/hex over 30 min) afforded 2.51 g (38.7%) 3-benzyloxy-5-bromo-1H-pyridin-2-one. LCMS [M+H]+=280.1

後処理

  1. temperatureAfter cooling
  2. customthe volatiles were removed in vacuo, 20 mL water and 40 mL EtOAc
  3. additionwere added
  4. extractionthe aqueous phase was extracted 2× with 20 mL EtOAc
  5. dry with materialThe combined organics were dried over Na2SO4
  6. customevaporated
  7. customPurification by automated flash chromatography (80 g silica gel cartridge 0-100% EtAOc/hex over 30 min)

出典と根拠

ORDレコード
ord-a5ebfeaab74c46c395fba64175c26cb5
出典データセット
uspto-grants-2016_04
特許番号
US09309199B2

反応ノート

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