Benzyl Alcohol → 3-(Benzyloxy)-5-bromopyridine

HRID 244583

반응식

HRID 244583 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.[CH2:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:9]([O:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5995293-Bromo-5-hydroxypyridine

생성물 1

HCID 153891983-(Benzyloxy)-5-bromopyridine수율 31.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a vial is added 3-bromo-5-hydroxypyridine (200 mg, 1.15 mmol), benzyl alcohol (137 mg, 1.27 mmol) and triphenylphosphine (332 mg, 1.27 mmol) in THF (5 ml) at 0° C., followed by the addition of diisopropyl azodicarboxylate (256 mg, 1.27 mmol). The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with EtOAc, washed with sat NaHCO3, water, brine, dried under anhy. Na2SO4, filtered and concentrated. The residue is purified by flash chromatography (SiO2, 0-5% MeOH/CH2Cl2) to afford title compound (97 mg); m/z 264.0, 266.0 [M, M+2H]

후처리

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionThe residue is diluted with EtOAc
  3. washwashed
  4. customdried under anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography (SiO2, 0-5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-dee370fb0bb64f7abb21b48bbf5c10cd
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658661B2

연결된 노트

불러오는 중…