Water → HCID 18388321、化合物

HRID 1936859ノート

反応式

HRID 1936859 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 18388321HCID 18388321、化合物収率 83.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24d4462c7e2747b9aaffa54f5716c218
出典データセット
uspto-grants-2002_05
特許番号
US06391905B1

反応ノート

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