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

HRID 1697200Notes

Reaction equation

HRID 1697200 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.CCOC(C)=O.CCCCCC>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

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 82115Trimethylsilyl cyanideHCID 21226206Ethyl acetate hexaneHCID 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, O-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

Sources & evidence

ORD record
ord-8e176fae00d54cf39ef7c91e2db7817a
Source dataset
uspto-grants-2012_04
Patent number
US08163909B2

Reaction notes

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