Formic Acid → 5-Ethoxycarbonylfuran-2-ylacetic acid

HRID 517327노트

반응식

HRID 517327 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 698426325-Ethoxycarbonylfuran-2-ylacetic acid

시약·촉매·용매 1

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

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d4044127998548c698cb29c9f07ac67e
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115107B2

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