Methanamine, N-methoxy-, hydrochloride (1:1) → 4,4,N-Trimethoxy-N-methylbutyramide

HRID 2196854

반응식

HRID 2196854 반응식
[CH3:1][O:2][CH:3]([O:10][CH3:11])[CH2:4][CH2:5][C:6]([O:8]C)=O.Cl.[CH3:13][NH:14][O:15][CH3:16].C([Mg]Cl)(C)C>C1COCC1>[CH3:11][O:10][CH:3]([O:2][CH3:1])[CH2:4][CH2:5][C:6]([N:14]([O:15][CH3:16])[CH3:13])=[O:8]

참가 물질

5

반응물 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 350846Methyl 4,4-dimethoxybutanoateHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 597880834,4,N-Trimethoxy-N-methylbutyramide수율 100.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

To a solution of methyl 4,4-dimethoxy-butyrate (4.99 g, 30.8 mmol) and N,O-dimethylhydroxylamine HCl (4.65 g, 47.68 mmol) in 60 mL of THF at −20° C., is added isopropylmagnesiumchloride (46 mL, 92.28 mmol, 2.0M in THF) maintaining the temperature below −20° C. After stirring at −10° C. for 30 min, the reaction mixture is quenched with 50 mL of water and extracted with 3×80 mL of EtOAc. The combined organic layers is dried over Na2SO4 and filtered through a short silica gel pluge. The solution is concentrated to give 4,4,N-Trimethoxy-N-methyl-butyramide (5.9 g, 99%) as pale liquid. M/Z=191.0

후처리

  1. temperaturemaintaining the temperature below −20° C
  2. customthe reaction mixture is quenched with 50 mL of water
  3. extractionextracted with 3×80 mL of EtOAc
  4. dry with materialThe combined organic layers is dried over Na2SO4
  5. filtrationfiltered through a short silica gel pluge
  6. concentrationThe solution is concentrated

출처 및 근거

ORD 기록
ord-8d8d11905634430f88025f1c87d402c0
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338440B2

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