Imidazole → 4-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylcyclohexanecarboxamide

HRID 1506136노트

반응식

HRID 1506136 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH2:4][CH2:3]1.N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20].O>CN(C)C=O>[Si:23]([O:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH2:4][CH2:3]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:25])[CH3:24]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 86642922HCID 86642922, 화합물

생성물 1

HCID 231446014-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylcyclohexanecarboxamide수율 73.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Hydroxy-N-methoxy-N-methylcyclohexanecarboxamide (7.34 g, 39.2 mmol) in N,N-dimethylformamide (200 mL) was stirred with imidazole (4.80 g, 70.6 mmol) and tert-butylchlorodimethylsilane (7.70 g, 51.0 mmol) at room temperature for one day. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=25/1→4/1 (v/v)) to give the title compound as a colorless oil (8.68 g, yield 73%).

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=25/1→4/1 (v/v))

출처 및 근거

ORD 기록
ord-340dcc6da55340cf868b1649c8a47626
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216999B2

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