Dimethylformamide → 5-(1,3-Dioxolan-2-yl)picolinaldehyde

HRID 640438ノート

反応式

HRID 640438 の反応式
[O:1]1CCC[CH2:2]1.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[CH:9][N:8]=1.C([Li])CCC.CN(C)C=O>O>[O:14]1[CH2:15][CH2:16][O:17][CH:13]1[C:10]1[CH:11]=[CH:12][C:7]([CH:2]=[O:1])=[N:8][CH:9]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 184696682-Bromo-5-(1,3-dioxolan-2-YL)pyridineHCID 178418339Butyllithium

生成物 1

HCID 592551735-(1,3-Dioxolan-2-yl)picolinaldehyde収率 47%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-78 °C

実験手順

To a tetrahydrofuran (100 mL) solution of 2-bromo-5-[1,3]dioxolan-2-yl-pyridine (4.77 g, 20.7 mmol) described in Manufacturing Example 154-1-2 was added n-butyl lithium (14.3 mL, 1.6 M hexane solution, 22.8 mmol) under nitrogen atmosphere at −78° C., which was stirred for 20 minutes at −78° C. Then, N,N-dimethylformamide (1.92 mL, 24.8 mmol) was added to the reaction mixture, which was stirred for 15 minutes while the temperature was raised to room temperature. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (1.73 g, 47%).

後処理

  1. stirringwas stirred for 15 minutes while the temperature
  2. temperaturewas raised to room temperature
  3. extractionwhich was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-3eb09899d8354bb3994e62bc14e8d9c2
出典データセット
uspto-grants-2010_04
特許番号
US07691882B2

反応ノート

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