Methoxymethylbutanol → N-hydroxy-3-methoxy-3-methylbutan-1-imine

HRID 475534

반응식

HRID 475534 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25]([CH3:30])([CH3:29])[CH2:26][CH2:27]O.COC(C)(C)CC=O.Cl.[OH:40][NH2:41]>C(OCC)(=O)C.N1C=CC=CC=1.C(Cl)(Cl)Cl>[OH:40][N:41]=[CH:27][CH2:26][C:25]([O:24][CH3:23])([CH3:30])[CH3:29]

참가 물질

8

반응물 4

HCID 62118MethoxymethylbutanolHCID 159087TriacetoxyperiodinaneHCID 443297Hydroxyamine hydrochlorideHCID 111709493-Methoxy-3-methylbutanal

생성물 1

HCID 86670070N-hydroxy-3-methoxy-3-methylbutan-1-imine수율 38.2%

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6212Chloroform용매2회HCID 8857Ethyl Acetate용매

실험 절차

Dess-Martin reagent (15.0 g) was added to a chloroform solution (35 ml) of 3-methoxy-3-methyl-1-butanol (3.3 g) under ice cooling and stirred at room temperature for 5 hours. Chloroform was added to the reaction mixture and the organic layer was washed with an aqueous solution of 20 wt. % sodium thiosulfate, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure, thereby obtaining a crude product containing 3-methoxy-3-methylbutanal. Hydroxyamine hydrochloride (3.5 g) was added to a pyridine solution of the obtained crude product (30 ml) under ice cooling and stirred at room temperature overnight under nitrogen atmosphere. Ethyl acetate was added to the reaction mixture and the organic layer was washed with water, 1M-hydrochloric acid aqueous solution and saturated brine. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (KP-Sil, Biotage, ethyl acetate/n-hexane=10 to 50%), thereby obtaining (N-hydroxy-3-methoxy-3-methylbutan-1-imine (1.4 g) as a colorless oily substance.

후처리

  1. washthe organic layer was washed with an aqueous solution of 20 wt. % sodium thiosulfate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customobtaining a crude product
  5. customobtained crude product (30 ml) under ice cooling
  6. stirringstirred at room temperature overnight under nitrogen atmosphere
  7. washthe organic layer was washed with water, 1M-hydrochloric acid aqueous solution and saturated brine
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by column chromatography (KP-Sil, Biotage, ethyl acetate/n-hexane=10 to 50%)

출처 및 근거

ORD 기록
ord-69f858a680a946669bf50bcfe03079b8
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637557B2

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