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

HRID 244583

反応式

HRID 244583 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 153891983-(Benzyloxy)-5-bromopyridine収率 31.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]

後処理

  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)

出典と根拠

ORDレコード
ord-dee370fb0bb64f7abb21b48bbf5c10cd
出典データセット
uspto-grants-2014_02
特許番号
US08658661B2

関連ノート

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