Toluene → 2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide

HRID 1841643ノート

反応式

HRID 1841643 の反応式
[CH2:1](Br)[C:2]#[CH:3].[C:5]1(C)[CH:10]=CC=C[CH:6]=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:34])[C:20]([NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([O:32][CH3:33])[CH:26]=2)=[O:21])=[CH:15][CH:14]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([O:34][CH2:10][C:5]#[CH:6])[C:20]([NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:1][C:2]#[CH:3])=[C:27]([O:32][CH3:33])[CH:26]=2)=[O:21])=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 112459552-(4-Bromophenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-acetamide

生成物 1

HCID 234468012-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒

実験手順

A 80% solution of propargyl bromide in toluene (10.5 g, 71 mmol) is added slowly at room temperature to a mixture of 2-(4-bromo-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide (11 g, 29 mmol), 30% sodium hydroxide solution (14 ml, 0.14 mol) and catalytic amounts of tetrabutylammonium bromide in 40 ml of dichloromethane. The reaction mixture is stirred for 16 hours at +40° C. Subsequently the mixture is evaporated and the residue is diluted with water and dichloromethane. The organic phase is separated and the aqueous layer is extracted three times with dichloromethane. The combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 1:1) to yield 2-(4-bromo-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide. 1H-NMR (300 MHz, CDCl3): 2.51 (t, 1H, C≡CH), 2.54 (t, 1H, C≡CH), 2.81 (t, 2H, CH2CH2), 3.54 (t, 2H, CH2CH2), 3.86 (s, 3H, OCH3), 3.97 (dd, 1H, OCH2), 4.20 (dd, 1H, OCH2), 4.78 (d, 2H, OCH2), 4.96 (s, 1H, CHOH), 6.70-7.52 (m, 8H, CH arom., NH).

後処理

  1. customSubsequently the mixture is evaporated
  2. additionthe residue is diluted with water and dichloromethane
  3. customThe organic phase is separated
  4. extractionthe aqueous layer is extracted three times with dichloromethane
  5. washThe combined organic phases are washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 1:1)

出典と根拠

ORDレコード
ord-9f9f78b4dab44e00b9d05577f8dfd807
出典データセット
uspto-grants-2004_01
特許番号
US06683211B1

反応ノート

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