Triethylamine → 1-Ethyl-5-(ethylthio)carbonyloxypyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone

HRID 1257990

반응식

HRID 1257990 반응식
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:25])=[C:7]([C:15]([C:17]2[CH:18]=[N:19][N:20]([CH2:23][CH3:24])[C:21]=2[OH:22])=[O:16])[CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])=[O:4].C(N(CC)CC)C.[CH3:33][CH2:34][S:35][C:36](Cl)=[O:37]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:25])=[C:7]([C:15]([C:17]2[CH:18]=[N:19][N:20]([CH2:23][CH3:24])[C:21]=2[O:22][C:36]([S:35][CH2:34][CH3:33])=[O:37])=[O:16])[CH:8]=[CH:9][C:10]=1[S:11]([CH3:14])(=[O:13])=[O:12])=[O:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18056Ethyl chlorothioformateHCID 178463120HCID 178463120, 화합물

생성물 1

HCID 872334581-Ethyl-5-(ethylthio)carbonyloxypyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone수율 66.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

5-Hydroxy-1-ethylpyrazol-4-yl 3-(methoxycarbonyl)-2-methyl-4-(methylsulfonyl)phenyl ketone (510 mg, 1.39 mmol) was dissolved in dry tetrahydrofuran (20 mL), and triethylamine (281 mg, 2.78 mmol) was added thereto. A solution (4 mL) of 96% S-ethyl chlorothiolformate (217 mg) dissolved in dry tetrahydrofuran was added thereto little by little under cooling with ice water. The reaction mixture was stirred for 90 minutes while the reaction temperature was allowed to warm to room temperature. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4) to obtain the desired product as an oil (417 mg, 0.92 mmol) (yield: 66%).

후처리

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:4)

출처 및 근거

ORD 기록
ord-757f210f2a244a8e9407f512046a958a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466088B2

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