Dimethylformamide → 2,4-Bis-methoxymethoxy-6-methoxymethyl-benzaldehyde

HRID 1798080노트

반응식

HRID 1798080 반응식
Br[C:2]1[C:7]([CH2:8][O:9][CH3:10])=[CH:6][C:5]([O:11][CH2:12][O:13][CH3:14])=[CH:4][C:3]=1[O:15][CH2:16][O:17][CH3:18].[Li]CCCC.CN([CH:27]=[O:28])C>CCOCC>[CH3:18][O:17][CH2:16][O:15][C:3]1[CH:4]=[C:5]([O:11][CH2:12][O:13][CH3:14])[CH:6]=[C:7]([CH2:8][O:9][CH3:10])[C:2]=1[CH:27]=[O:28]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 582927852-Bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzeneHCID 178418339Butyllithium

생성물 1

HCID 582925712,4-Bis-methoxymethoxy-6-methoxymethyl-benzaldehyde수율 81.3%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 2-bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene (10.5 g, 32.8 mmol) in Et2O (100 mL) was treated with n-BuLi (28.7 mL, 71.9 mmol) at −78° C. for 1 h. Then, DMF (27.7 mL, 359 mmol) was added to the reaction and the resulting mixture was warmed to room temperature for 3 h. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=2:1) affording the title compound (7.21 g). 1H NMR (300 MHz, CD3OD) δ 10.49 (s, 1H), 7.46 (s, 1H), 6.45 (s, 1H), 5.27 (s, 2H), 5.24 (s, 2H), 4.83 (s, 2H), 3.51 (s, 3H). 3.50 (s, 3H), 3.49 (s, 3H).

후처리

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-2706003124ed465f98405ba942f32c0d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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