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Triphenylphosphine → Methyl 5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoate

HRID 1251908
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HRID 1251908 반응식
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[OH:9])[CH:6]=1.[F:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][CH2:21][C:22]2[CH:31]=[CH:30][C:29](O)=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[O:9][C:29]2[CH:30]=[CH:31][C:22]([CH2:21][CH2:20][C:19]3[CH:18]=[CH:17][C:16]([F:15])=[CH:34][CH:33]=3)=[C:23]([CH:28]=2)[C:24]([O:26][CH3:27])=[O:25])[CH:6]=1
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 183244462-(4-Methylimidazol-1-yl)-1-(thiazol-2-yl)ethanolHCID 18324453Methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate

생성물 1

HCID 18324416Methyl 5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoate수율 48.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A stirred mixture of 2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethanol (1.35 g, 6.46 mM), methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate (1.95 g, 7.1 mM) and triphenylphosphine (1.86 g, 7.1 mM) in dry THF was cooled in an ice bath, and treated with DEAD (1.24 g, 7.1 mM). The mixture was allowed to warm to ambient temperature, stirred for 18 hours and evaporated to dryness. The product was purified on silica using methanol/dichloromethane (3→10%) as eluant to give methyl 5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoate (1.45 g, 48%).

후처리

  1. temperaturewas cooled in an ice bath
  2. customevaporated to dryness
  3. customThe product was purified on silica

출처 및 근거

ORD 기록
ord-099796db366b411fa995b630272b4b02
출처 데이터셋
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06342765B1

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