Chloromethyl Methyl Ether → Diethyl 1-(methoxymethyl)-2,5-dioxo-4-imidazolylphosphonate

HRID 1033113

反応式

HRID 1033113 の反応式
[O:1]=[C:2]1[N:6]=[C:5]([P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[C:4](=[O:15])[NH:3]1.[H-].[Na+].[CH3:18][O:19][CH2:20]Cl>CN(C=O)C.CCOCC.C(OCC)(=O)C>[CH3:18][O:19][CH2:20][N:3]1[C:4](=[O:15])[C:5]([P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[N:6][C:2]1=[O:1]

参加物

7

反応物 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 53733419Diethyl (2,5-dioxo-2,5-dihydro-1H-imidazol-4-yl)phosphonate

生成物 1

HCID 53791991Diethyl 1-(methoxymethyl)-2,5-dioxo-4-imidazolylphosphonate

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of diethyl 2,5-dioxo-4-imidazolylphosphonate (3.61 g, 0.015 moles) in DMF (10 mL), under N2, is added sodium hydride (80% dispersion in oil) (0.55 g, 0.018 moles) and stirred for 5 minutes. Chloromethyl methyl ether (tech. grade 85%) (1.9 mL, 0.021 moles) is added. This mixture is stirred at room temperature for 4 hours, diluted with ether and ethyl acetate (300 mL) and then washed with water and brine before drying over MgSO4. The aqueous layer is back extracted with methylene chloride and combined with the previous organic fraction. Evaporation of solvents and chromatography (eluant 1% methanol in chloroform) and evaporation under high vacuum affords the required product.

後処理

  1. stirringThis mixture is stirred at room temperature for 4 hours
  2. washwashed with water and brine
  3. dry with materialbefore drying over MgSO4
  4. extractionThe aqueous layer is back extracted with methylene chloride
  5. customEvaporation of solvents and chromatography (eluant 1% methanol in chloroform) and evaporation under high vacuum

出典と根拠

ORDレコード
ord-b827a0970433490393d7126541b0b1b2
出典データセット
uspto-grants-1994_05
特許番号
US05308853

関連ノート

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