Nitrogen → 6-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridinecarboxaldehyde

HRID 2064964ノート

反応式

HRID 2064964 の反応式
N#N.Br[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[N:5]=1.[Li]CCCC.CN([CH:24]=[O:25])C.C([O-])(O)=O.[Na+]>CCOCC.CCCCCC>[CH3:15][C:10]1([C:6]2[N:5]=[C:4]([CH:24]=[O:25])[CH:9]=[CH:8][CH:7]=2)[O:14][CH2:13][CH2:12][O:11]1

参加物

8

反応物 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 121642822-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridineHCID 178418339Butyllithium

生成物 1

HCID 860859206-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridinecarboxaldehyde

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-bromo-6-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (2.21 g, 9.05 mmol) in Et2O (60.0 mL) at −78° C. was added dropwise n-BuLi (3.70 mL of a 2.5M solution in hexane, 9.25 mmol). The reaction mixture was then stirred at −78° C. for 30 min before DMF (0.85 mL, 11.00 mmol) was added dropwise. The reaction mixture was allowed to warm to rt over 1 h. 5% aq. NaHCO3 was added and the mixture was extracted three times with Et2O. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA to pure EA) gave the title compound as a pale yellow solid.

後処理

  1. additionwas added dropwise
  2. extractionthe mixture was extracted three times with Et2O
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (4:1 hept-EA to pure EA)

出典と根拠

ORDレコード
ord-00c723701142415ca5fca446fe7c609b
出典データセット
uspto-grants-2012_10
特許番号
US08288419B2

反応ノート

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