Acetone → 2-(6-Bromo-3-pyridyl)-2-propanol

HRID 447102ノート

反応式

HRID 447102 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.C([Li])CCC.[CH3:14][C:15]([CH3:17])=[O:16]>C1COCC1.CCOCC>[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:15]([OH:16])([CH3:17])[CH3:14])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 180AcetoneHCID 47382712-Bromo-5-iodopyridineHCID 178418339Butyllithium

生成物 1

HCID 223919732-(6-Bromo-3-pyridyl)-2-propanol収率 64%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To 2-bromo-5-iodo-pyridine (2.974 g, 10.2 mmol) in a mixture of THF (15 mL) and ether (20 mL) at −78° C. is added dropwise n-butyl lithium (2.5 M in hexane, 4 L, 10.2 mmol). The mixture is stirred at −78° C. for 30 min, then acetone (anhydrous, 0.749 uL, 10.2 mmol) is added drop wise. The mixture is slowly warmed up to −50° C. over 1.5 h and is quenched with saturated ammonium chloride, extracted with ethyl acetate. The organic phase is separated, dried and rotavaped. The residue is purified by silica gel chromatography (10-20% ethyl acetate in heptane) to give the title compound as white solid (1.40 g, 64%).

後処理

  1. temperatureThe mixture is slowly warmed up to −50° C. over 1.5 h
  2. customis quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is separated
  5. customdried
  6. customThe residue is purified by silica gel chromatography (10-20% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-39dc9628389d4183910b1593ed075198
出典データセット
uspto-grants-2013_07
特許番号
US08481542B2

反応ノート

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