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Hydrochloric Acid → 6-(Pyridin-2-yloxymethyl)-pyridine-3-carbaldehyde

HRID 640441
ノート
印刷プレビュー

反応式

HRID 640441 の反応式
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[CH:8][C:9]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:10][CH:11]=1.CS(C)=O.Cl.[OH-].[Na+]>O1CCCC1>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH2:12][C:9]1[N:10]=[CH:11][C:6]([CH:2]=[O:1])=[CH:7][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 592553385-[1,3]Dioxolan-2-yl-2-(pyridin-2-yloxymethyl)-pyridine

生成物 1

HCID 592553126-(Pyridin-2-yloxymethyl)-pyridine-3-carbaldehyde収率 48.1%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of 5-[1,3]dioxolan-2-yl-2-(pyridin-2-yloxymethyl)-pyridine (1.51 g, 5.85 mmol) described in Manufacturing Example 154-1-5 in tetrahydrofuran (15 mL) and dimethyl sulfoxide (10 mL) was added a 5 N hydrochloric acid aqueous solution (3 mL), which was stirred for 25 minutes at room temperature, and then for another 1 hour at 20 minutes at 60° C. A 5 N sodium hydroxide aqueous solution 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=1:1) to obtain the title compound (603 mg, 48%).

後処理

  1. waitfor another 1 hour at 20 minutes at 60° C
  2. extractionwhich was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-0c296f5640a6474d9ef666d0a4d95379
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07691882B2

反応ノート

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