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

HRID 640185

반응식

HRID 640185 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
-78 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-fb51133b094b4dbb9e2c11db99abf14f
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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