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

HRID 974000노트

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HRID 974000 반응식
[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

참가 물질

7

반응물 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 57052728N-(4-dimethylamino-2-butynyl)benzoylformamideHCID 178418573HCID 178418573, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-85164694e30145108a31e54a27703f1a
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05066680

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