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Ethanol → 2-(6-Fluoroquinolin-2-yl)ethanol

HRID 920888
ノート
印刷プレビュー

反応式

HRID 920888 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[OH-].[Na+].C=O.C[CH2:18][OH:19]>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:18][OH:19])[CH:6]=[CH:5]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 702EthanolHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 707846-Fluoro-2-methylquinoline

生成物 1

HCID 836745642-(6-Fluoroquinolin-2-yl)ethanol収率 30.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

6-Fluoro-2-methylquinoline (1.00 g, 6.20 mmol) and sodium hydroxide were each added sequentially to the mixture of HCHO in water. Then 2 mL of EtOH were added to the mixture. The resulting solution was stirred at about 85° C. overnight. The organic layer was extracted with EA (3×10 mL), collected and dried with anhydrous Na2SO4, filtered and concentrated to afford a pink oil. The crude material was purified by chromatography on silica-gel (eluent: PE/EA=6/1) and then further purified by combi-flash chromatography (NH4HCO3/H2O, MeOH/H2O=40%-60%) to give 360 mg of the title product (yield: 30.3%).

後処理

  1. extractionThe organic layer was extracted with EA (3×10 mL)
  2. customcollected
  3. dry with materialdried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a pink oil
  7. customThe crude material was purified by chromatography on silica-gel (eluent: PE/EA=6/1)
  8. customfurther purified by combi-flash chromatography (NH4HCO3/H2O, MeOH/H2O=40%-60%)

出典と根拠

ORDレコード
ord-9d5a1de7af2a4998b6cc81a8e44567c4
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09273068B2

反応ノート

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