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

HRID 77897

반응식

HRID 77897 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]=[C:17]([CH3:19])[CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.C([Li])CCC.CN(C)C=O>O>[CH3:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([O:12][CH2:11][C:10]2[CH:20]=[CH:21][C:7]([CH:2]=[O:1])=[CH:8][CH:9]=2)[CH:18]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 592552882-(4-Bromo-benzyloxy)4-methyl-pyridineHCID 178418339Butyllithium

생성물 1

HCID 592554674-(4-Methyl-pyridin-2-yloxymethyl)-benzaldehyde수율 55.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
-78 °C

실험 절차

To a tetrahydrofuran (150 mL) solution of 2-(4-bromo-benzyloxy)-4-methyl-pyridine (5.70 g, 20.5 mmol) described in Manufacturing Example 43-1-1 was added dropwise n-butyl lithium (2.67 M n-hexane solution, 9.21 mL, 24.6 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere, which was stirred for 20 minutes at −78° C. N,N-dimethylformamide (3.16 mL, 41.0 mmol) was then added dropwise thereto and stirred for 10 minutes at −78° C. The reaction solution was allowed to room temperature, water was added, and the solution was 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=1:3) to obtain the title compound (2.58 g, 55.4%).

후처리

  1. stirringstirred for 10 minutes at −78° C
  2. customwas allowed to room temperature
  3. extractionthe solution was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:3)

출처 및 근거

ORD 기록
ord-a322369c707e495283faa3205c06efcf
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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