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

HRID 1854658ノート

反応式

HRID 1854658 の反応式
[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]

参加物

8

反応物 3

HCID 7864Chloromethyl Methyl Ether2 回HCID 81531Diisopropylethylamine2 回HCID 872934-(Diethylamino)-2-hydroxybenzaldehyde

生成物 1

HCID 143876754-Diethylamino-2-(methoxymethoxy)benzaldehyde収率 88.3%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒2 回HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-b6645accd21b40f99225f507b10365a7
出典データセット
uspto-grants-2015_02
特許番号
US08962674B2

反応ノート

読み込み中…