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

HRID 1691264
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HRID 1691264 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c066c4e3f2e148bba08bf60aadc869d3
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08153662B2

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