Ethylene Glycol → 2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine

HRID 42782노트

반응식

HRID 42782 반응식
N#N.[Br:3][C:4]1[N:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1.[CH2:13](O)[CH2:14][OH:15].COC(OC)OC.C([O-])([O-])=O.[Na+].[Na+]>>[Br:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:10]2([CH3:11])[O:15][CH2:14][CH2:13][O:12]2)[N:9]=1

참가 물질

6

반응물 5

HCID 174Ethylene GlycolHCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 112985782-Acetyl-6-bromopyridine

생성물 1

HCID 121642822-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine

반응 조건

온도
95 °C

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(6-bromo-pyridin-2-yl)-ethanone (1880 mg, 9.40 mmol) in ethylene glycol (10.00 mL, 179.32 mmol) was treated with trimethylorthoformate (2.10 mL, 19.16 mmol) followed by LiBF4 (180 mg, 1.88 mmol). The reaction mixture was heated at 95° C. for 5 h. Sat. aq. Na2CO3 was added and the mixture was extracted twice with ether and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 hept-EA) gave the title compound as a pale yellow oil: TLC:rf (50:50 hept-EA)=0.57.

후처리

  1. extractionthe mixture was extracted twice with ether
  2. dry with materialthe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the residue by FC (20:1 hept-EA)

출처 및 근거

ORD 기록
ord-886bb6659579497e863c091669bff0b7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

반응 노트

불러오는 중…