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

HRID 1841643노트

반응식

HRID 1841643 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9f9f78b4dab44e00b9d05577f8dfd807
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06683211B1

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