Dimethylformamide → 4-(5-Methyl-pyridin-2-yloxymethyl)-benzaldehyde

HRID 1691009

反応式

HRID 1691009 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[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)=[CH:9][CH:8]=1.C([Li])CCC.CN(C)C=O>O>[CH3:19][C:16]1[CH:17]=[CH:18][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]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 592554492-(4-Bromo-benzyloxy)-5-methyl-pyridineHCID 178418339Butyllithium

生成物 1

HCID 592551424-(5-Methyl-pyridin-2-yloxymethyl)-benzaldehyde収率 66.5%

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 (150 mL) solution of 2-(4-bromo-benzyloxy)-5-methyl-pyridine (5.40 g, 19.4 mmol) described in Manufacturing Example 44-1-1 was added dropwise n-butyl lithium (2.67 M n-hexane solution, 8.73 mL, 23.3 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere, which was stirred for 30 minutes at −78° C. N,N-dimethylformamide (2.99 mL, 38.8 mmol) was then added dropwise thereto, which was stirred for 10 minutes at −78° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was separated and washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:6→1:4) to obtain the title compound (2.93 g, 66.5%).

後処理

  1. stirringwhich was stirred for 10 minutes at −78° C
  2. extractionwhich was then extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:6→1:4)

出典と根拠

ORDレコード
ord-be9e824a0a2f42f490d8043571c75972
出典データセット
uspto-grants-2012_04
特許番号
US08153662B2

関連ノート

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