Chloromethyl Methyl Ether → 4-Diethylamino-2-(methoxymethoxy)benzaldehyde

HRID 1854658노트

반응식

HRID 1854658 반응식
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([OH:12])[CH:5]=1)[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:24][O:25][CH2:26]Cl>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.Cl>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([O:12][CH2:24][O:25][CH3:26])[CH:5]=1)[CH3:14]

참가 물질

8

반응물 3

HCID 7864Chloromethyl Methyl Ether2회HCID 81531Diisopropylethylamine2회HCID 872934-(Diethylamino)-2-hydroxybenzaldehyde

생성물 1

HCID 143876754-Diethylamino-2-(methoxymethoxy)benzaldehyde수율 88.3%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매2회HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

4-Diethylamino-2-hydroxybenzaldehyde (300 mg, 1.55 mmol) was placed in a 20 mL reaction vessel, and dissolved in 4.7 mL of dry dichloromethane. To the solution were added N,N-diisopropylethylamine (0.40 mL, 2.3 mmol), 4-dimethylaminopyridine (13 mg, 0.11 mmol), and chloromethyl methyl ether (147 μL, 1.94 mmol). After the reaction mixture was stirred at room temperature overnight, N,N-diisopropylethylamine (0.40 mL, 2.3 mmol), 4-dimethylaminopyridine (13 mg, 0.11 mmol), and chloromethyl methyl ether (147 μL, 1.94 mmol) were added again with additional stirring for 3 h. The resulting mixture was diluted with 100 mL of ethyl acetate and 20 mL of 1N HCl, and extracted. The extract was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a pale yellow oil (324.7 mg, 88%).

후처리

  1. stirringwith additional stirring for 3 h
  2. extractionextracted
  3. washThe extract was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-b6645accd21b40f99225f507b10365a7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962674B2

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