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Methanol → 2-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehyde

HRID 505661
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HRID 505661 반응식
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C)[CH:27]=[O:28].O.CO>C(OCC)C>[CH2:18]([O:17][CH2:16][C:3]1[CH:4]=[C:5]([O:12][CH2:13][O:14][CH3:15])[CH:6]=[C:7]([O:8][CH2:9][O:10][CH3:11])[C:2]=1[CH:27]=[O:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
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참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 6228DimethylformamideHCID 231475942-Bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene

생성물 1

HCID 216698172-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehyde수율 72%

시약·촉매·용매 1

HCID 3283Diethyl Ether
용매

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온도
-78 °C

실험 절차

The above-obtained 2-bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene (1.6 g, 4.3 mmol) was dissolved in diethylether (25 mL) and cooled to −78° C. The obtained solution was added with 1.52 mol/L n-butyllithium-hexane solution (4.0 mL, 6.1 mmol) and stirred at −78° C. for 1 hour. Then, N,N-dimethylformamide (1.0 mL, 13 mmol) was added thereto and stirred at a room temperature for 3 hours. The reaction mixture was added with water and methanol, and then extracted with chloroform 3 times. The organic layers were combined, washed with saturated brine, and then dried over anhydrous sodium sulfate. Then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 to 5/1 to 3/1) to obtain 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehyde (0.99 g, 72%).

후처리

  1. additionThe obtained solution was added with 1.52 mol/L n-butyllithium-hexane solution (4.0 mL, 6.1 mmol)
  2. stirringstirred at a room temperature for 3 hours
  3. extractionextracted with chloroform 3 times
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThen the solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 to 5/1 to 3/1)

출처 및 근거

ORD 기록
ord-4f6fedc485ba409ca1005d609e123232
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07781485B2

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