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

HRID 1039671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039671
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b7eb11250c92458c801856d9b37e2e05
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552181B2

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