Diethyl Ether → 2-(2-Chloro-5-fluoropyrimidin-4-yl)propan-2-ol

HRID 338065ノート

反応式

HRID 338065 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[C:5]([F:11])=[CH:4][N:3]=1.[CH3:12][Mg]Br.C(OCC)C>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])([CH3:12])[CH3:9])[C:5]([F:11])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 865947381-(2-Chloro-5-fluoropyrimidin-4-yl)ethanoneHCID 178418573HCID 178418573、化合物

生成物 1

HCID 866978842-(2-Chloro-5-fluoropyrimidin-4-yl)propan-2-ol収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A stirred, −78° C. solution of 1-(2-chloro-5-fluoro-pyrimidin-4-yl)ethanone (10.06 g, 57.6 mmol) in tetrahydrofuran (100 mL) under nitrogen is reacted with a 3 M solution of methyl magnesium bromide in diethyl ether (124 mL, 72.04 mmol) and the resulting mixture is stirred at −78° C. for 20 minutes. The reaction is quenched with aqueous saturated ammonium chloride and the mixture is warmed to room temperature. The reaction mixture is extracted three times with ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated under vacuum. The crude product is purified over silica gel with a 30 minute, 5% to 100% ethyl acetate in hexanes gradient, to give the title compound (7.06 g, 64%). ES/MS (m/e): (35Cl/37Cl) 191/193 (M+H).

後処理

  1. customThe reaction is quenched with aqueous saturated ammonium chloride
  2. temperaturethe mixture is warmed to room temperature
  3. extractionThe reaction mixture is extracted three times with ethyl acetate
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product is purified over silica gel with a 30 minute

出典と根拠

ORDレコード
ord-5609727a6b934b1b957d7da1f1fae8c2
出典データセット
uspto-grants-2014_11
特許番号
US08889856B2

反応ノート

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