Cesium carbonate → (2-Methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-phenoxy)-acetic acid tert-butyl ester

HRID 1242308ノート

反応式

HRID 1242308 の反応式
Cl[CH:2]([C:4]1[C:5]([CH3:20])=[N:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)[CH3:3].[C:21]([O:25][C:26](=[O:40])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]C(=O)C)=[CH:31][C:30]=1[CH3:39])([CH3:24])([CH3:23])[CH3:22].C(OC(=O)COC1C=CC(S)=CC=1C)(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.CO>[C:21]([O:25][C:26](=[O:40])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35][CH:2]([C:4]2[C:5]([CH3:20])=[N:6][C:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)=[CH:8][CH:9]=2)[CH3:3])=[CH:31][C:30]=1[CH3:39])([CH3:24])([CH3:23])[CH3:22]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 11572955(4-Acetylsulfanyl-2-methyl-phenoxy)-acetic acid tert-butyl esterHCID 21935947[Rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 67072235(4-Mercapto-2-methyl-phenoxy)-acetic acid tert-butyl ester

生成物 1

HCID 67072330(2-Methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-phenoxy)-acetic acid tert-butyl ester収率 54.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

実験手順

0.224 g (0.75 mmol) of [rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine and 0.222 g (0.75 mmol) of (4-acetylsulfanyl-2-methyl-phenoxy)-acetic acid tert-butyl ester (prepared by standard acetylation of (4-mercapto-2-methyl-phenoxy)-acetic acid tert-butyl ester, described below in example 28A)-C]) were dissolved in 3.9 ml of acetonitrile and 0.2 ml of MeOH and treated with 0.292 g (1.2 eq.) of Cs2CO3. The reaction was then allowed to proceed over night. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9/1), afforded in the less polar fractions 0.210 g of pure title compound and in the more polar fractions 0.112 g of the corresponding methyl ester as waxy solid.

後処理

  1. waitto proceed over night
  2. additionPouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents

出典と根拠

ORDレコード
ord-968dc1aa0be344afac3905b975d49e93
出典データセット
uspto-grants-2006_10
特許番号
US07115611B2

反応ノート

読み込み中…