Diethyl Ether → 2-(5-Bromo-3-pyridyl)propan-2-ol

HRID 705069

반응식

HRID 705069 반응식
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Br:10])[CH:9]=1)(=[O:3])[CH3:2].[CH3:11][Mg]Br.C(OCC)C>O1CCCC1>[Br:10][C:8]1[CH:9]=[C:4]([C:1]([OH:3])([CH3:11])[CH3:2])[CH:5]=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 8204233-Acetyl-5-bromopyridineHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cooled (−78° C.) solution of 3-acetyl-5-bromo pyridine (1.98 g, 9.90 mmol) in tetrahydrofuran (33 mL) was added dropwise a solution of methyl magnesium bromide in diethyl ether (3.0 M, 6.60 mL, 19.8 mmol). The reaction was warmed to room temperature, and the resulting mixture was stirred at room temperature overnight. The reaction was then quenched with saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organic extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-60% ethyl acetate in hexanes) provided the title compound: LCMS m/z 217.83 [M+11]+; 1H NMR (500 MHz, CDCl3) δ 8.61 (s, 1H), 8.53 (s, 1H), 8.01 (d, J=1.9 Hz, 1H), 2.38 (br s, 1H), 1.61 (6H).

후처리

  1. customThe reaction was then quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel (0-60% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-83eeb3bbb294465dae11bfec4f09120d
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173873B2

연결된 노트

불러오는 중…