Water → 4-Methoxy-5-methyl-6-(5-benzyloxy-1-ethylpyrazol-4-yl) carbonylthiochroman-1,1-dioxide

HRID 1458251노트

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HRID 1458251 반응식
[CH3:1][O:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:14]([C:16]3[CH:17]=[N:18][N:19]([CH2:22][CH3:23])[C:20]=3[OH:21])=[O:15])[C:11]=2[CH3:13])[S:6](=[O:25])(=[O:24])[CH2:5][CH2:4]1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:1][O:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:14]([C:16]3[CH:17]=[N:18][N:19]([CH2:22][CH3:23])[C:20]=3[O:21][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:15])[C:11]=2[CH3:13])[S:6](=[O:24])(=[O:25])[CH2:5][CH2:4]1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178418308HCID 178418308, 화합물

생성물 1

HCID 221018874-Methoxy-5-methyl-6-(5-benzyloxy-1-ethylpyrazol-4-yl) carbonylthiochroman-1,1-dioxide수율 74%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

4-Methoxy-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl) carbonylthiochroman-1,1-dioxide was used as a starting material (XIH). And, 0.4 g (1.10 mmol) thereof was dissolved in 5 ml of acetone, and 0.21 g (1.21 mmol) of benzyl bromide as a reaction reagent (XII) and 0.15 g (1.10 mmol) of potassium carbonate as a base were added. The resultant mixture was refluxed under heat for 3 hours. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. Its organic layer was separated, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the resultant oil was purified with flush column chromatography (Wako Gel C-300: hexane/ethyl acetate=2:3) to give 0.37 g (yield 74%) of 4-methoxy-5-methyl-6-(5-benzyloxy-1-ethylpyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound No. 62) as an end compound which comes under the general formula (XI). Table 21 shows the structures of the starting material (XIH) and the reaction reagent (XII), and the structure and the yield of the end product (I).

후처리

  1. temperatureunder heat for 3 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. customIts organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. customthe resultant oil was purified
  7. customwith flush column chromatography (Wako Gel C-300: hexane/ethyl acetate=2:3)

출처 및 근거

ORD 기록
ord-314c49cd9f4840d4a14c31d0a2d5b644
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849926

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