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

HRID 552797Notes

Reaction equation

HRID 552797 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-59e166574c2648f9bdad1204e61ad446
Source dataset
uspto-grants-2011_05
Patent number
US07951838B2

Reaction notes

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