Benzoyl chloride → 3-(Methoxymethoxy)-6-neopentylpicolinonitrile

HRID 1039671노트

반응식

HRID 1039671 반응식
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N+:9]([O-])[CH:10]=1.C(Cl)(=O)C1C=CC=CC=1.C[Si]([C:30]#[N:31])(C)C>C(Cl)Cl>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:10]([C:30]#[N:31])=[N:9][C:8]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 82115Trimethylsilyl cyanideHCID 671636565-(methoxymethoxy)-2-neopentylpyridine-N-oxide

생성물 1

HCID 671656733-(Methoxymethoxy)-6-neopentylpicolinonitrile수율 74%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-(Methoxymethoxy)-2-neopentylpyridine-N-oxide (11.5 g, 51 mmol) was dissolved in CH2Cl2 (50 mL) to which benzoyl chloride (12 ml, 102 mmol) and (trimethylsilyl)formonitrile (14 ml, 102 mmol) were added. The mixture was stirred under N2 4 h, quenched with saturated NaHCO3 (150 mL), and extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with saturated NaHCO3 (2×50 mL), dried (MgSO4), and evaporated to give the crude product as a brown oil, which was purified by ISCO (330 g SiO2, 0-40% EtOAc/Hexane) to give 3-(methoxymethoxy)-6-neopentylpicolinonitrile (8.8 g, 74% yield) as a clear oil.

후처리

  1. additionwere added
  2. customquenched with saturated NaHCO3 (150 mL)
  3. extractionextracted with CH2Cl2 (3×100 mL)
  4. washThe combined organic layers were washed with saturated NaHCO3 (2×50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give the crude product as a brown oil, which
  8. customwas purified by ISCO (330 g SiO2, 0-40% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-b7eb11250c92458c801856d9b37e2e05
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552181B2

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