Formic Acid → 5-Ethoxycarbonylfuran-2-ylacetic acid

HRID 517327ノート

反応式

HRID 517327 の反応式
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11]Cl)=[CH:9][CH:10]=1)=[O:5])[CH3:2].[I-].[K+].[CH:15]([OH:17])=[O:16]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][C:15]([OH:17])=[O:16])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 284Formic AcidHCID 4875Potassium IodideHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

生成物 1

HCID 698426325-Ethoxycarbonylfuran-2-ylacetic acid

試薬・触媒・溶媒 1

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-触媒

反応条件

温度
75 °C

実験手順

5-Chloromethyl-2-furancarboxylic acid ethyl ester (1.0 g, 5.3 mmol), potassium iodide (0.044 g, 0.27 mmol), and chloro(1,5-cyclooctadiene)rhodium(I) dimer (0.26 g, 0.53 mmol) were dissolved in formic acid (25 mL), and the mixture was stirred at 75° C. for 6 hours under a carbon monoxide atmosphere. The solvent was evaporated, and the residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the solvent was evaporated, and the residue was purified by silica gel column chromatography to give the title compound (0.61 g).

後処理

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d4044127998548c698cb29c9f07ac67e
出典データセット
uspto-grants-2015_08
特許番号
US09115107B2

反応ノート

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