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Water → Ethyl 3-[1-[3,5-bis(2-phenyl-4-thiazolylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate

HRID 350261
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HRID 350261 반응식
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:26]=[C:27]([OH:29])[CH:28]=1)[CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9]1.Cl[CH2:31][C:32]1[N:33]=[C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[S:35][CH:36]=1.O>CN(C)C=O>[C:37]1([C:34]2[S:35][CH:36]=[C:32]([CH2:31][O:3][C:4]3[CH:5]=[C:6]([CH:26]=[C:27]([O:29][CH2:31][C:32]4[N:33]=[C:34]([C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)[S:35][CH:36]=4)[CH:28]=3)[CH2:7][N:8]3[CH:12]=[C:11]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:10]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9]3)[N:33]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleHCID 23024867Ethyl 3-[1-(3,5-dihydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate

생성물 1

HCID 69423991Ethyl 3-[1-[3,5-bis(2-phenyl-4-thiazolylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate수율 28.8%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

Sodium hydride (601, oily, 0.30 g) was added to a solution of ethyl 3-[1-(3,5-dihydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate (1.83 g) in N,N-dimethylformamide (20 ml) at 0° C., and the mixture was stirred at room temperature for 15 minutes. 4-Chloromethyl-2-phenylthiazole (1.05 g) was added to the mixture and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 3-[1-[3,5-bis(2-phenyl-4-thiazolylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate (513 mg, yield: 14%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

후처리

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-77d7e27089314603a1a8851fa30cb14b
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07179823B1

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