Allyl bromide → 2-allyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide

HRID 643236ノート

反応式

HRID 643236 の反応式
[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][CH:6]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]#[CH:21])=[C:14]([O:22][CH3:23])[CH:13]=1)=[O:8].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:1]([O:5][CH:6]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]#[CH:21])=[C:14]([O:22][CH3:23])[CH:13]=1)=[O:8])[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 592605842-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide

生成物 1

HCID 592605832-allyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒

実験手順

Allyl bromide (1.2 g, 10 mmol) is added slowly at room temperature to a mixture of 2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide (3.0 g, 8.2 mmol), 30% sodium hydroxide solution (6.5 ml, 41 mmol) and catalytic amounts of tetrabutylammonium bromide (50 mg) in 30 ml of dichloromethane. The reaction is stirred for 16 hours at +40° C. Subsequently the mixture is evaporated and the residue is diluted with water and dichloromethane. The phases are separated and the aqueous phase is extracted three times with dichloromethane. The combined organic layer is 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 give 2-allyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-3-p-tolyl-propionamide (E1.17).

後処理

  1. customSubsequently the mixture is evaporated
  2. additionthe residue is diluted with water and dichloromethane
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted three times with dichloromethane
  5. washThe combined organic layer is 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-7b2d5379a07e4769a2a07c0e199e8ffc
出典データセット
uspto-grants-2010_04
特許番号
US07700522B2

反応ノート

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