Dimethylformamide → 5-(Dimethoxymethyl)picolinaldehyde

HRID 885837노트

반응식

HRID 885837 반응식
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:16][CH3:17])[O:14][CH3:15])=[CH:9][N:8]=1.CN([CH:21]=[O:22])C>CCCCCC.C1COCC1.O>[CH3:15][O:14][CH:13]([O:16][CH3:17])[C:10]1[CH:11]=[CH:12][C:7]([CH:21]=[O:22])=[N:8][CH:9]=1

참가 물질

7

반응물 3

HCID 6228DimethylformamideHCID 64252132-Bromo-5-(dimethoxymethyl)pyridineHCID 178418339Butyllithium

생성물 1

HCID 184267805-(Dimethoxymethyl)picolinaldehyde수율 53.7%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
-70 °C

실험 절차

A solution of 2.5 M BuLi in hexane (7.6 ml) was added drop-wise, under a N2 atmosphere, to a solution of 2-bromo-5-dimethoxymethyl-pyridine (3.66 g, 15.84 mmol) in THF (60 ml) at −70° C. After 15 minutes, DMF (1.82 ml, 23.5 mmol) was added drop-wise and the mixture was stirred for 30 minutes at −70° C. and then allowed to reach room temperature. The reaction was diluted with H2O and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated to dryness in vacuo. The crude product was purified by flash chromatography (petroleum ether: AcOEt 7:3) to obtain 1.54 g of 5-dimethoxymethyl-pyridine-2-carbaldehyde as a yellow oil.

후처리

  1. customat −70° C
  2. customto reach room temperature
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customThe crude product was purified by flash chromatography (petroleum ether: AcOEt 7:3)

출처 및 근거

ORD 기록
ord-dfebf1fb641e4b699ce82772e6849100
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242175B2

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