Dimethylformamide → 4-(3-Fluoro-pyridin-2-yloxymethyl)-benzaldehyde

HRID 1691254ノート

反応式

HRID 1691254 の反応式
[O:1]1CCC[CH2:2]1.Br[C:7]1[CH:21]=[CH:20][C:10]([CH2:11][O:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.C([Li])CCC.CN(C)C=O>O>[F:19][C:18]1[C:13]([O:12][CH2:11][C:10]2[CH:20]=[CH:21][C:7]([CH:2]=[O:1])=[CH:8][CH:9]=2)=[N:14][CH:15]=[CH:16][CH:17]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 592552352-(4-Bromo-benzyloxy)-3-fluoro-pyridineHCID 178418339Butyllithium

生成物 1

HCID 592552614-(3-Fluoro-pyridin-2-yloxymethyl)-benzaldehyde収率 53%

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 (40 mL) solution of 2-(4-bromo-benzyloxy)-3-fluoro-pyridine (2.03 g, 7.20 mmol) described in Manufacturing Example 149-1-1 was added n-Butyl lithium (5.04 mL, 1.6 M hexane solution, 7.92 mmol) under nitrogen atmosphere at −78° C., which was stirred for 45 minutes at −78° C. Then, N,N-dimethylformamide (725 μL, 9.36 mmol) was added to the reaction mixture at −78° C., which was stirred for 1 hour and 10 minutes while the temperature was raised to room temperature. Water was added to the reaction solution 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 residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (887 mg, 53%).

後処理

  1. stirringwhich was stirred for 1 hour and 10 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. 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-feaa763558e74b04bf22f9921aca196e
出典データセット
uspto-grants-2012_04
特許番号
US08153662B2

反応ノート

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