Hydrochloric Acid → 5-Acetylfuro(2,3-c)pyridine

HRID 1251564노트

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HRID 1251564 반응식
[O:1]=[C:2]([C:8]1[CH:9]=[C:10]2[CH:16]=[CH:15][O:14][C:11]2=[CH:12][N:13]=1)[CH2:3]C(OC)=O.O=C(C1C=C2C=COC2=CN=1)CC(OCC)=O.O=C(C1C=C2C=COC2=CN=1)CC(OC(C)(C)C)=O.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:2]([C:8]1[CH:9]=[C:10]2[CH:16]=[CH:15][O:14][C:11]2=[CH:12][N:13]=1)(=[O:1])[CH3:3]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9859266Methyl beta-oxo-5-furo[2,3-c]pyridinepropionateHCID 18324176Ethyl beta-oxo-5-furo[2,3-c]pyridinepropionateHCID 18324178Tert-butyl beta-oxo-5-furo[2,3-c]pyridinepropionate

생성물 1

HCID 97939025-Acetylfuro(2,3-c)pyridine수율 78%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
60 °C

실험 절차

The 971 mg of the mixture of methyl β-oxo-5-furo[2,3-c]pyridinepropionate, ethyl β-oxo-5-furo[2,3-c]pyridinepropionate, and tert-butyl β-oxo-5-furo[2,3-c]pyridinepropionate (molar ratio of 55:44:1) obtained in Example 9 was dissolved in 20 mL of toluene, and 1.04 g of 35% hydrochloric acid was added at room temperature with stirring. After addition, the reaction mixture was heated to 60° C., and a reaction was carried out for 3 hours with stirring. The reaction solution was then cooled to room temperature and was neutralized with 8.40 g of 5% sodium hydroxide aqueous solution. The organic layer was separated, the aqueous layer was extracted twice with 5 mL of methylene chloride, and the combined organic layer was dried with anhydrous magnesium sulfate and then concentrated in a rotary evaporator. The resulting solids were recrystallized from a mixed solvent of toluene-hexane, giving 629 mg of 5-acetylfuro[2,3-c]pyridine in a purity of 99% by HPLC (78% yield from 5-ethoxycarbonylfuro[2,3-c]pyridine).

후처리

  1. additionAfter addition
  2. stirringwith stirring
  3. temperatureThe reaction solution was then cooled to room temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with 5 mL of methylene chloride
  6. dry with materialthe combined organic layer was dried with anhydrous magnesium sulfate
  7. concentrationconcentrated in a rotary evaporator
  8. customThe resulting solids were recrystallized from a mixed solvent of toluene-hexane

출처 및 근거

ORD 기록
ord-d768c3b1eb2a45df8eca97b1edc3596e
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06342606B2

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