Nitrogen → 4-(2-Methyl-[1,3]dioxolan-2-yl)-pyridine-2-carbaldehyde

HRID 2064986노트

반응식

HRID 2064986 반응식
N#N.Br[C:4]1[CH:9]=[C:8]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[CH:7]=[CH:6][N:5]=1.[Li]CCCC.CN([CH:24]=[O:25])C.[NH4+].[Cl-]>CCOCC>[CH3:15][C:10]1([C:8]2[CH:7]=[CH:6][N:5]=[C:4]([CH:24]=[O:25])[CH:9]=2)[O:14][CH2:13][CH2:12][O:11]1

참가 물질

7

반응물 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 866494792-Bromo-4-(2-methyl-[1,3]dioxolan-2-yl)-pyridineHCID 178418339Butyllithium

생성물 1

HCID 866494804-(2-Methyl-[1,3]dioxolan-2-yl)-pyridine-2-carbaldehyde

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-bromo-4-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (520 mg, 2.13 mmol) in dry Et2O (15 mL) was added n-BuLi (0.85 mL of a 2.5M solution in hexanes, 2.13 mmol) at −78° C. The reaction mixture was then stirred for 30 min at −78° C. before DMF (0.2 mL, 2.58 mmol) was added dropwise. The reaction mixture was allowed to warm up to rt and stirred at this temperature for 10 min. Sat. aq. NH4Cl (10 mL) was added, the layers separated and the aq. layer extracted with Et2O (3×10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (10:1 to 2:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (1:1 hept-EA)=0.30.

후처리

  1. additionwas added dropwise
  2. customthe layers separated
  3. extractionthe aq. layer extracted with Et2O (3×10 mL)
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customPurification of the residue by FC (10:1 to 2:1 hept-EA)

출처 및 근거

ORD 기록
ord-f24ebe81e775490eb0df91be73b72307
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288419B2

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