Water → Tolpyralate

HRID 452366

反応式

HRID 452366 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:26])=[C:8]([C:16]([C:18]2[CH:19]=[N:20][N:21]([CH2:24][CH3:25])[C:22]=2[OH:23])=[O:17])[CH:9]=[CH:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].[C:33](=[O:40])([O:38][CH3:39])[O:34][CH:35](Cl)[CH3:36].O>CC(=O)CC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:33](=[O:40])([O:38][CH3:39])[O:34][CH:35]([O:23][C:22]1[N:21]([CH2:24][CH3:25])[N:20]=[CH:19][C:18]=1[C:16](=[O:17])[C:8]1[CH:9]=[CH:10][C:11]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[C:7]=1[CH3:26])[CH3:36]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 135066411-Chloroethyl methyl carbonateHCID 178463133HCID 178463133、化合物

生成物 1

HCID 44473182Tolpyralate収率 47.4%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

5-Hydroxy-1-ethylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (300 mg) was dissolved in 2-butanone (10 mL), and potassium carbonate (130 mg) and tetrabutylammonium bromide (15 mg) were added. After stirring at room temperature for 10 minutes, 1-chloroethyl methyl carbonate (purity: 85%, 270 mg) was added at room temperature, followed by heating and refluxing for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and poured into water and then extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and a saturated sodium chloride aqueous solution, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography with n-hexane:ethyl acetate=1:1, to obtain the desired product (180 mg) as slightly yellow solid. The NMR spectrum data of this product are as follows.

後処理

  1. temperatureby heating
  2. temperaturerefluxing for 3 hours
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled to room temperature
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 1N hydrochloric acid
  7. dry with materialby drying over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe obtained residue was purified by column chromatography with n-hexane

出典と根拠

ORDレコード
ord-9b6fd4b205ac4a88ba051d9c4f4791d4
出典データセット
uspto-grants-2013_07
特許番号
US08492310B2

関連ノート

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