Toluene → N-[4-dimethylamino-2-butynyl)-2-hydroxy-2-methyl-2-phenylacetamide

HRID 974000ノート

反応式

HRID 974000 の反応式
[CH3:1][Mg]Br.[CH3:4][N:5]([CH3:21])[CH2:6][C:7]#[C:8][CH2:9][N:10](C(=O)C1C=CC=CC=1)[CH:11]=[O:12].[OH-:22].[Na+].[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)C.O1CCCC1>[CH3:21][N:5]([CH3:4])[CH2:6][C:7]#[C:8][CH2:9][NH:10][C:11](=[O:12])[C:30]([OH:22])([CH3:1])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 57052728N-(4-dimethylamino-2-butynyl)benzoylformamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 15023479N-[4-dimethylamino-2-butynyl)-2-hydroxy-2-methyl-2-phenylacetamide

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

A solution of methylmagnesium bromide (10.23 m mol) in diethyl ether (3.5 ml) and tetrahydrofuran (5 ml) were added to a solution of N-(4-dimethylamino-2-butynyl)-benzoylformamide (0.50 g) in toluene (8 ml) at room temperature. After being heated at 70° C. for 1.5 hours, the mixture was treated with 1N aqueous solution of sodium hydroxide and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (15:1) as an eluent to give N-[4-dimethylamino-2-butynyl)-2-hydroxy-2-methyl-2-phenyl-acetamide (0.21 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (15:1) as an eluent

出典と根拠

ORDレコード
ord-85164694e30145108a31e54a27703f1a
出典データセット
uspto-grants-1991_11
特許番号
US05066680

反応ノート

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