N,N,N',N'-Tetramethylethylenediamine → (3-Chloro-2-methoxymethoxyphenyl)(2-methoxymethoxyphenyl)methanol

HRID 466932

반응식

HRID 466932 반응식
C([Li])CCC.CN(C)CCN(C)C.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][O:23][CH3:24].[CH3:25][O:26][CH2:27][O:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH:31]=[O:32]>CCCCCC.O1CCCC1>[Cl:14][C:15]1[C:16]([O:21][CH2:22][O:23][CH3:24])=[C:17]([CH:31]([C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[O:28][CH2:27][O:26][CH3:25])[OH:32])[CH:18]=[CH:19][CH:20]=1

참가 물질

7

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 5426241-Chloro-2-(methoxymethoxy)benzeneHCID 108774852-(Methoxymethoxy)benzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 19812669(3-Chloro-2-methoxymethoxyphenyl)(2-methoxymethoxyphenyl)methanol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A 1.6M solution of n-butyl lithium in hexane (140 ml) was placed in a 1 l flask and cooled in an ice bath. To this was added with stirring 34 ml of tetramethylethylenediamine and, after a 10 min reaction period, 34.5 g of 1-chloro-2-methoxymethoxybenzene (dropwise over a 30 min period). A pale orange suspension formed and this was stirred for 4 hours continuing the ice bath cooling. A solution of 34.5 g of 2-methoxymethoxybenzaldehyde in 30 ml of tetrahydrofuran was added with stirring and cooling. The reaction was exothermic. When the addition was complete, the mixture was allowed to warm to room temperature and was then quenched carefully with water. The resulting mixture was poured into a mixture of 1 l of ethyl acetate and 500 ml of aqueous ammonium chloride. The phases were separated and the organic phase was extracted twice with water and once with brine, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a viscous, pale orange oil. This was purified by filtration chromatography, eluting with mixtures of hexane and dichloromethane starting with pure hexane and ending with pure dichloromethane, to obtain 52.2 g (77 percent of theory) of the title compound as a pale yellow oil. The proton and carbon NMR and infrared spectra were consistent with the assigned structure.

후처리

  1. temperaturecooled in an ice bath
  2. additionTo this was added
  3. customA pale orange suspension formed
  4. temperaturecooling
  5. stirringwith stirring
  6. temperaturecooling
  7. additionWhen the addition
  8. customwas then quenched carefully with water
  9. additionThe resulting mixture was poured into a mixture of 1 l of ethyl acetate and 500 ml of aqueous ammonium chloride
  10. customThe phases were separated
  11. extractionthe organic phase was extracted twice with water and once with brine
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated by evaporation under reduced pressure
  15. customto obtain a viscous, pale orange oil
  16. filtrationThis was purified by filtration chromatography
  17. washeluting with mixtures of hexane and dichloromethane starting with pure hexane

출처 및 근거

ORD 기록
ord-a21853dddf7944e7ad1fc4c089ffb133
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05158597

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