Benzyl Alcohol → 5-Formyl-2-furancarboxylic acid benzyl ester

HRID 34097

反応式

HRID 34097 の反応式
[CH:1]([C:3]1[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1)=[O:2].C(N(CC)CC)C.ClC(OCC)=O.[CH2:24](O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.O>[CH2:24]([O:9][C:8]([C:6]1[O:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1)=[O:10])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 27937195-Formyl-2-furancarboxylic Acid

生成物 1

HCID 600347885-Formyl-2-furancarboxylic acid benzyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

500 mg of 5-formylfuran-2-carboxylic acid was dissolved in 10 mL of tetrahydrofuran, added with 990 μl of triethylamine, cooled to 0° C., and then added with 374 μl of ethyl chloroformate. After stirring at this temperature for 30 minutes, 406 μl of benzylalcohol was added and stirred at room temperature overnight. Adding water to stop the reaction, the solution was extracted with ethyl acetate. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and purified by silica gel column chromatography, to afford 508 mg of the title compound as white crystals.

後処理

  1. stirringstirred at room temperature overnight
  2. customthe reaction
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic phase was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-dfac25dd13174f6c8780d2cc80446cf2
出典データセット
uspto-grants-2008_09
特許番号
US07429609B2

関連ノート

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