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

HRID 490770

反応式

HRID 490770 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-1e39dc89aa9343e1bbf5e362de2afa7f
出典データセット
uspto-grants-2009_05
特許番号
US07528160B2

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