Ethyl Acetate → {2-(3-Hydroxy-4-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

HRID 1161390ノート

反応式

HRID 1161390 の反応式
[CH3:1][O:2][C:3](=[O:41])[N:4]=[C:5]([S:39][CH3:40])[C:6]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][Si](C(C)C)(C(C)C)C(C)C)[CH:21]=1)=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[CH3:1][O:2][C:3](=[O:41])[N:4]=[C:5]([S:39][CH3:40])[C:6]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([OH:28])[CH:21]=1)=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 72312841{2-(4-Methoxy-3-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

生成物 1

HCID 72312763{2-(3-Hydroxy-4-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester収率 72.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 2724141Tetrabutylammonium Fluoride溶媒

実験手順

After dissolving 3.52 g of {2-(4-methoxy-3-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 50 ml of THF, 6.49 ml of TBAF (1.0 M, THF solution) was added and the mixture was stirred at room temperature for 15 hours. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (1.88 g, isomeric mixture) as a light yellow solid.

後処理

  1. additionwas added
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

出典と根拠

ORDレコード
ord-cd28a05609574d69ada0025ee620c52c
出典データセット
uspto-grants-2010_10
特許番号
US07816522B2

反応ノート

読み込み中…