Water → 5-(Dimethoxymethyl)picolinaldehyde

HRID 1281144노트

반응식

HRID 1281144 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:11][CH3:12])[O:9][CH3:10])=[CH:4][N:3]=1.C([Mg]Cl)(C)C.CN(C)[CH:20]=[O:21].O>O1CCCC1>[CH3:10][O:9][CH:8]([O:11][CH3:12])[C:5]1[CH:6]=[CH:7][C:2]([CH:20]=[O:21])=[N:3][CH:4]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 64252132-Bromo-5-(dimethoxymethyl)pyridineHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 184267805-(Dimethoxymethyl)picolinaldehyde수율 44.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-bromo-5-dimethoxymethylpyridine (1.19 g, 5.13 mmol) in tetrahydrofuran (8 mL) was added isopropylmagnesium chloride (2 mol/L in tetrahydrofuran; 4.2 mL, 8.4 mmol) under nitrogen atmosphere, and the mixture was stirred at room temperature for 3 h. Dimethylformamide (0.774 mL, 10.3 mmol) was added, and the mixture was stirred for additional 10 min. Water was added, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (5:1 to 3:1 hexane/ethyl acetate) to afford 5-dimethoxymethyl-2-pyridinecarboxaldehyde (413 mg, 44%).

후처리

  1. stirringthe mixture was stirred for additional 10 min
  2. extractionthe mixture was extracted with ethyl acetate twice
  3. washThe organic layer was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (5:1 to 3:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-9e8dca299e84413fafc408b49443f0d6
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06452014B1

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