2,6-Lutidine → 3-Bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)pyridine

HRID 1013527

反応式

HRID 1013527 の反応式
FC(F)(F)S([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])(=O)=O.N1C(C)=CC=CC=1C.[Br:24][C:25]1[CH:26]=[C:27]([CH2:31]O)[CH:28]=[N:29][CH:30]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:24][C:25]1[CH:30]=[N:29][CH:28]=[C:27]([CH2:31][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[CH:26]=1

参加物

6

反応物 4

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 2784733(5-Bromo-3-pyridinyl)methanol

生成物 1

HCID 219840913-Bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)pyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Tert-butyldimethylsilyl trifluoromethanesulfonate (1.174 ml, 5.11 mmol) was added to 2,6-lutidine (0.743 ml, 6.38 mmol) and (5-bromopyridin-3-yl)methanol (800 mg, 4.25 mmol) stirred in CH2Cl2 (10 ml) cooled to 0° C. and the mixture was stirred at 0° C. for 1 h. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture and the mixture was extracted with ethyl acetate. The combined organic fractions were dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography to provide 3-bromo-5-({[tertbutyl(dimethyl)silyl]oxy}methyl)pyridine: MS: cal'd 325 (MNa+), exp 325 (MNa+).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic fractions were dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-ff87c445d7e44a4fb060c83b735553f1
出典データセット
uspto-grants-2011_07
特許番号
US07981874B2

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