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

HRID 1798058노트

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HRID 1798058 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 82.7%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
-78 °C

실험 절차

To a solution of 2-bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene (5.66 g, 17.59 mmol) in Et2O (60 mL) was added n-BuLi (15.47 mL, 2.5 M in Hexane) at −78° C. After stirring for 1 hour at −78° C., DMF (13.6 mL, 175.8 mmol) was the added and reaction mixture was allowed to warm to room temperature over 3 hours. The reaction was quenched with saturated NH4Cl and extracted with Et2O. The organic extracts were dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 2,4-bis-methoxymethoxy-6-methoxymethyl-benzaldehyde (3.93 g, 82%). 1H NMR (400 MHz, CDCl3δ 10.50 (s, 1H), 7.03 (s, 1H), 6.77 (s, 1H), 5.30 (s, 2H), 5.27 (s, 2H), 4.80 (s, 3H), 3.50 (s, 3H), 4.49 (s, 3H).

후처리

  1. additionadded
  2. customreaction mixture
  3. temperatureto warm to room temperature over 3 hours
  4. customThe reaction was quenched with saturated NH4Cl
  5. extractionextracted with Et2O
  6. customThe organic extracts were dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash column chromatography

출처 및 근거

ORD 기록
ord-2ffb4afab5834de892ca0971f1354952
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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