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

HRID 131574

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HRID 131574 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 66144Ethyl bromopyruvate2회HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 75263Isopropyl Isothiocyanate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-76c525657b4847d8834fd30940cac0cc
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384950B2

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