Dimethylformamide → 5-(Dimethoxymethyl)picolinaldehyde

HRID 885837ノート

反応式

HRID 885837 の反応式
[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

参加物

7

反応物 3

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

生成物 1

HCID 184267805-(Dimethoxymethyl)picolinaldehyde収率 53.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dfebf1fb641e4b699ce82772e6849100
出典データセット
uspto-grants-2012_08
特許番号
US08242175B2

反応ノート

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