Water → 4-(6-Methyl-pyridin-2-yloxymethyl)-benzaldehyde

HRID 77805

反応式

HRID 77805 の反応式
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:24]=[O:25].O>O1CCCC1.C(OCC)(=O)C>[CH3:14][C:10]1[N:9]=[C:8]([O:7][CH2:6][C:5]2[CH:15]=[CH:16][C:2]([CH:24]=[O:25])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1

参加物

7

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 592554782-(4-Bromo-benzyloxy)-6-methyl-pyridineHCID 178418339Butyllithium

生成物 1

HCID 592551484-(6-Methyl-pyridin-2-yloxymethyl)-benzaldehyde収率 70.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2-(4-bromo-benzyloxy)-6-methyl-pyridine (7.30 g, 26.2 mmol) described in Manufacturing Example 3-1-1 in anhydrous tetrahydrofuran (200 mL) was added dropwise n-butyl lithium (2.67 M n-hexane solution, 11.8 mL, 31.4 mmol) on a dry ice-ethanol bath (−78° C.), which was stirred for 30 minutes at −78° C. N,N-dimethylformamide (4.04 mL, 52.4 mmol) was added to this mixture at −78° C., and stirred for 5 minutes. Water and ethyl acetate were added to the reaction mixture, which was stirred for 10 minutes at room temperature, and the organic layer was then separated. This organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3) to obtain the title compound (4.19 g, 70%).

後処理

  1. stirringstirred for 5 minutes
  2. stirringwas stirred for 10 minutes at room temperature
  3. customthe organic layer was then separated
  4. washThis organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3)

出典と根拠

ORDレコード
ord-9d2a2f695a4546a7b606bf2d9ffb1460
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

読み込み中…