Tributylphosphine → (6-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-benzofuran-3-yl)-acetic acid methyl ester

HRID 490770

반응식

HRID 490770 반응식
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][CH2:18][OH:19].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.C(P(CCCC)CCCC)CCC.[CH3:51][O:52][C:53](=[O:65])[CH2:54][C:55]1[C:59]2[CH:60]=[CH:61][C:62](O)=[CH:63][C:58]=2[O:57][CH:56]=1>C1(C)C=CC=CC=1.O>[CH3:51][O:52][C:53](=[O:65])[CH2:54][C:55]1[C:59]2[CH:60]=[CH:61][C:62]([O:19][CH2:18][CH2:17][C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=4)[S:6][C:2]=3[CH3:1])=[CH:63][C:58]=2[O:57][CH:56]=1

참가 물질

7

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetateHCID 226474902-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol

생성물 1

HCID 57675482(6-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-benzofuran-3-yl)-acetic acid methyl ester수율 33%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

To a solution of 2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol (0.12 g, 0.43 mmol) in toluene (3 mL) at 0° C. is added ADDP (0.14 g, 0.57 mmol) followed by tri-n-butylphosphine (0.14 mL, 0.56 mmol). A toluene solution of (6-Hydroxy-benzofuran-3-yl)-acetic acid methyl ester (0.52 g, 1.22 mmol) is added, and the mixture is allowed to warm to RT overnight. Water is added, and the aqueous phase is extracted with EtOAc. The organics are dried with MgSO4 and purified by flash chromatography to yield the title compound (0.066 g, 33%).

후처리

  1. extractionthe aqueous phase is extracted with EtOAc
  2. dry with materialThe organics are dried with MgSO4
  3. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-1e39dc89aa9343e1bbf5e362de2afa7f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528160B2

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