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

HRID 530017

反応式

HRID 530017 の反応式
[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

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 8204233-Acetyl-5-bromopyridineHCID 178418573HCID 178418573、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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+H]+; 1H NMR (500 MHz, CDCl3) δ 8.61 (s, 1 H), 8.53 (s, 1 H), 8.01 (d, J=1.9 Hz, 1 H), 2.38 (br s, 1 H), 1.61 (6 H).

後処理

  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)

出典と根拠

ORDレコード
ord-9d68144ca2c048fe9759be13c9ba3edc
出典データセット
uspto-grants-2016_05
特許番号
US09351973B2

関連ノート

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