Water → Diethyl 2-((isopropyl)amino)thiophene-3,4-dicarboxylate

HRID 131574

反応式

HRID 131574 の反応式
[CH2:1]([O:3][C:4]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[CH:26]([N:29]=[C:30]=[S:31])([CH3:28])[CH3:27].Br[CH2:33][C:34](=O)[C:35]([O:37][CH2:38][CH3:39])=[O:36].O>C1COCC1>[CH:26]([NH:29][C:30]1[S:31][CH:33]=[C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])([CH3:28])[CH3:27]

参加物

6

反応物 4

HCID 962WaterHCID 66144Ethyl bromopyruvate2 回HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 75263Isopropyl Isothiocyanate

生成物 1

HCID 68818932Diethyl 2-((isopropyl)amino)thiophene-3,4-dicarboxylate収率 76.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Ethoxycarbonylmethylene triphenyl phosphorane (33.8 g) in dry THF (200 ml) was treated with isopropyl isothiocyanate (10.1 g) at 65° C. for 16 h under nitrogen. The mixture was cooled to −78° C. and ethyl bromo-pyruvate (19.5 g) was added. The reaction was allowed to warm slowly to room temperature. After 24 h at room temperature more ethyl bromo-pyruvate (3.17 g) was added and the mixture was stirred at room temperature for 16 h. The reaction was poured into water (1.5 L) and extracted into ether. Drying and evaporation gave an oil which was chromatographed (SiO2/5:1 isohexane-ethyl acetate) to afford the subtitle compound (21.2 g). δ 1HCDCl3 1.23-1.43 (12H, m), 3.46 (1H, m), 4.2-4.35 (4H, m), 6.50 (1H, s), 7.52 (1H, br.d)

後処理

  1. temperatureto warm slowly to room temperature
  2. extractionextracted into ether
  3. customDrying
  4. customevaporation
  5. customgave an oil which
  6. customwas chromatographed (SiO2/5:1 isohexane-ethyl acetate)

出典と根拠

ORDレコード
ord-76c525657b4847d8834fd30940cac0cc
出典データセット
uspto-grants-2008_06
特許番号
US07384950B2

関連ノート

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