Water → HCID 18388321, 화합물

HRID 1108331노트

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HRID 1108331 반응식
[CH:1]([S:4][C:5]1[S:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:7]2[CH2:15][CH2:16][CH2:17][C:18](=[O:19])[C:6]=12)([CH3:3])[CH3:2].[Br:20]Br.O>CO>[Br:20][CH:17]1[CH2:16][CH2:15][C:7]2=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:9][C:5]([S:4][CH:1]([CH3:2])[CH3:3])=[C:6]2[C:18]1=[O:19]

참가 물질

5

반응물 3

HCID 962WaterHCID 24408BromineHCID 2820027ethyl 4-oxo-3-propan-2-ylsulfanyl-6,7-dihydro-5H-2-benzothiophene-1-carboxylate

생성물 1

HCID 18388321HCID 18388321, 화합물수율 83.9%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

Ethyl 4,5,6,7-tetrahydro-3-isopropylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.50 g) was dissolved in methanol (80 ml); a solution of bromine (1.34 g) in methanol (8.6 ml) was added dropwise at room temperature. After the reaction mixture was stirred at room temperature for 2 hours, it was poured over water and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium thiosulfate, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:5, v/v) to yield ethyl 5-bromo-4,5,6,7-tetrahydro-3-isopropylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.65 g, 83.9%), which was then recrystallized from ethyl acetate-hexane. Colorless prisms. Melting point 107-108° C.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous solution of sodium thiosulfate
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. washeluted with ethyl acetate-hexane (1:5

출처 및 근거

ORD 기록
ord-b30a0a7415b84d8b8a999605f4e7fd7f
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066658

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