Acetone → 2-(6-Bromo-5-methoxypyridin-2-yl)propan-2-ol

HRID 658086

反応式

HRID 658086 の反応式
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4](I)[N:3]=1.C([Li])CCC.[CH3:16][C:17]([CH3:19])=[O:18].O>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([C:17]([OH:18])([CH3:19])[CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

参加物

8

反応物 4

HCID 180AcetoneHCID 962WaterHCID 110990402-Bromo-6-iodo-3-methoxypyridineHCID 178418339Butyllithium

生成物 1

HCID 575560732-(6-Bromo-5-methoxypyridin-2-yl)propan-2-ol

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-Bromo-6-iodo-3-methoxy-pyridine (500 mg) is dissolved in dry toluene (5 ml) and thereto is added dropwise 1.6M n-butyllithium in hexane (1 ml) at −78° C. under nitrogen atmosphere, and the mixture is stirred for 1 hour and thereto is added acetone (0.23 ml), and the mixture is stirred overnight. To the reaction solution are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→6:2) to give 2-(6-bromo-5-methoxy-pyridin-2-yl)-propan-2-ol (197 mg). MS (m/z): 246/248 [M+H]+

後処理

  1. stirringthe mixture is stirred overnight
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→6:2)

出典と根拠

ORDレコード
ord-1f6e356549924bf58356ad7926f353d7
出典データセット
uspto-grants-2011_12
特許番号
US08076364B2

関連ノート

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