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

HRID 473350ノート

反応式

HRID 473350 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 671656733-(Methoxymethoxy)-6-neopentylpicolinonitrile収率 74%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0fde6bd1a2de4325bd043d788dbbfd14
出典データセット
uspto-grants-2014_01
特許番号
US08633315B2

反応ノート

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