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Methyl cyanoacetate → Methyl 2-cyano-4-(2-fluorophenyl)-3-methyl-4-oxobutanoate

HRID 1962476
ノート
印刷プレビュー

反応式

HRID 1962476 の反応式
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].C(N(C(C)C)CC)(C)C.Br[CH:18]([CH3:28])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])=[O:20]>O1CCCC1>[C:1]([CH:3]([CH:18]([CH3:28])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])=[O:20])[C:4]([O:6][CH3:7])=[O:5])#[N:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7747Methyl cyanoacetateHCID 81531DiisopropylethylamineHCID 221113342-Bromo-1-(2-fluorophenyl)propan-1-one

生成物 1

HCID 66924807Methyl 2-cyano-4-(2-fluorophenyl)-3-methyl-4-oxobutanoate収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

To a solution of methyl cyanoacetate (15.5 mL) and diisopropylethylamine (64 mL) in tetrahydrofuran (110 mL) was added a solution of 2-bromo-1-(2-fluorophenyl)propan-1-one (36.8 g) in tetrahydrofuran (160 mL), and the mixture was stirred at 70° C. for 20 hr. The reaction mixture was allowed to cool to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=5:1) to give the title compound as a brown oil (yield 31.9 g, 80%).

後処理

  1. temperatureto cool to room temperature
  2. filtrationthe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-e0ec37f44f2d498d8d8907a733dd8c9b
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415368B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート