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

HRID 1386658ノート

反応式

HRID 1386658 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-56ccb9866b124c758e1f6814f80c87b2
出典データセット
uspto-grants-2001_07
特許番号
US06265580B1

反応ノート

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