Formic Acid → Furan-2,3-dicarbaldehyde

HRID 1830559

반응식

HRID 1830559 반응식
[O:1]1CCO[CH:2]1[C:6]1[O:7][CH:8]=[CH:9][C:10]=1[CH:11]=[O:12].C(O)=O.C([O-])(O)=O.[Na+].CCOC(C)=O>O>[O:7]1[CH:8]=[CH:9][C:10]([CH:11]=[O:12])=[C:6]1[CH:2]=[O:1]

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 220476222-(1,3-Dioxolan-2-yl)-3-furaldehyde

생성물 1

HCID 13814199Furan-2,3-dicarbaldehyde수율 114.1%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

2-(1,3-Dioxolan-2-yl)-3-furaldehyde (2.91 g, 17.31 mmol) is combined with formic acid (17 mL, 451 mmol) and water (4.25 mL) and stirred at rt for 18 h. The mixture is slowly transferred into a solution of NaHCO3 (45 g, 541 mmol) in water (600 mL), then stirred for 0.5 h. EtOAc (200 mL) is added, the layers separated and the aqueous layer extracted with EtOAc (2×200 mL). The combined organics are dried over Na2SO4 and concentrated to a yellow oil (3.28 g). The crude material is chromatographed over 90 g slurry-packed silica gel, eluting with 20% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 2.45 g of furan-2,3-dicarbaldehyde slightly contaminated with ethylene glycol diformate as a yellow oil. 1H NMR (CDCl3): δ 7.00, 7.67, 10.07, 10.49 ppm.

후처리

  1. stirringstirred for 0.5 h
  2. customthe layers separated
  3. extractionthe aqueous layer extracted with EtOAc (2×200 mL)
  4. dry with materialThe combined organics are dried over Na2SO4
  5. concentrationconcentrated to a yellow oil (3.28 g)
  6. customThe crude material is chromatographed over 90 g slurry-packed silica gel
  7. washeluting with 20% EtOAc/hexane
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5294a536fd254819adbbb9a11590d007
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067515B2

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