Carbon Dioxide → 1-methyl-3-pentafluoroethyl-1H-pyrazole-5-carboxylic acid

HRID 1843109노트

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HRID 1843109 반응식
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])=[N:3]1.C([N-]C(C)C)(C)C.[Li+].[C:22](=[O:24])=[O:23].[OH-].[Na+]>C(OCC)C.C1COCC1.CCCCCCC.O>[CH3:1][N:2]1[C:6]([C:22]([OH:24])=[O:23])=[CH:5][C:4]([C:7]([F:12])([F:13])[C:8]([F:9])([F:10])[F:11])=[N:3]1

참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 2724682Lithium diisopropylamideHCID 229722731-methyl-3-pentafluoroethyl-1H-pyrazole

생성물 1

HCID 148368761-methyl-3-pentafluoroethyl-1H-pyrazole-5-carboxylic acid수율 19.7%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 21263495Tetrahydrofuran heptane용매

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온도
-78 °C

실험 절차

Under an argon atmosphere, 5.00 g (24.99 mmol) of 1-methyl-3-pentafluoroethyl-1H-pyrazole are initially introduced in diethyl ether and the solution is cooled to −78° C. 11.09 ml (27.73 mmol) of 2M lithium diisopropylamide solution in THF/heptane are added dropwise and, at −30° C. with vigorous stirring, 450 g of crushed dry ice are added. When the evolution of gas has finished, the reaction mixture is admixed with 235 ml of water and adjusted to a pH of 11 with 1N sodium hydroxide solution. The alkaline solution is extracted three times with ethyl acetate and then adjusted to pH 2 with 1N hydrochloric acid. The aqueous phase is extracted three times with ethyl acetate and the organic phase is dried over sodium sulphate. Distilling off the solvent on a rotary evaporator under reduced pressure gives 1.20 g (17.75% of theory) of 1-methyl-3-pentafluoroethyl-1H-pyrazole-5-carboxylic acid as a solid.

후처리

  1. additionare added
  2. extractionThe alkaline solution is extracted three times with ethyl acetate
  3. extractionThe aqueous phase is extracted three times with ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. distillationDistilling off the solvent
  6. customon a rotary evaporator under reduced pressure

출처 및 근거

ORD 기록
ord-a023707af7ef45beae0c96f207a2211d
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946234B2

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