Water → 2-(3-Methyl-4-chloro-pyridin-2-yl)-2-cyclopropyl-acetaldehyde

HRID 1478301노트

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HRID 1478301 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([CH:12]2[CH2:14][CH2:13]2)=[CH:9][O:10]C)[C:3]=1[CH3:15].S(=O)(=O)(O)O.O.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH:12]2[CH2:14][CH2:13]2)[CH:9]=[O:10])[C:3]=1[CH3:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 669802244-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methylpyridine

생성물 1

HCID 186293552-(3-Methyl-4-chloro-pyridin-2-yl)-2-cyclopropyl-acetaldehyde수율 67.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To a solution of 4-chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methylpyridine (1.7 g, 7.60 mmol) in THF (15 mL) a 2M aqueous solution of sulfuric acid (15.20 mL, 30.4 mmol) was added and the reaction mixture was stirred at 50° C. for a total of 2.5 h. The resulting mixture was poured into water and neutralized with a saturated sodium bicarbonate solution, and thereafter, extracted with chloroform (3×20 mL). The resulting organic layers were washed with saturated salt water (20 mL), dried over sodium sulfate and concentrated under reduced pressure. The resulting yellow solid was purified by silica gel column chromatography (hexane:ethyl acetate) (4:1) to obtain the aldehyde (1.08 g, 67.8%).

후처리

  1. extractionextracted with chloroform (3×20 mL)
  2. washThe resulting organic layers were washed with saturated salt water (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting yellow solid was purified by silica gel column chromatography (hexane:ethyl acetate) (4:1)

출처 및 근거

ORD 기록
ord-6c91271efa8f4c36ace3e7919fcfdf19
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403818B2

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