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

HRID 1843077ノート

反応式

HRID 1843077 の反応式
[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+]>O1CCCC1.CCCCCCC.O.C(OCC)C>[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 21263495Tetrahydrofuran heptane溶媒

反応条件

温度
-78 °C

実験手順

Under an argon atmosphere, 5.00 g (25.0 mmol) of 1-methyl-3-pentafluoroethyl-1H-pyrazole are initially introduced into diethyl ether and the solution is cooled to −78° C. 11.1 ml (27.7 mmol) of 2M lithium diisopropylamide solution in tetrahydrofuran/heptane are added dropwise and, at −30° C. and with vigorous stirring, 450 g of crushed dry ice are added. When the evolution of gas has stopped, the reaction mixture is admixed with 235 ml of water and adjusted to pH 11 with 1M 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 of the solvent on a rotary evaporator under reduced pressure gives 1.20 g of 1-methyl-3-pentafluoroethyl-1H-pyrazole-5-carboxylic acid (18%) as a solid.

後処理

  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 of the solvent on a rotary evaporator under reduced pressure

出典と根拠

ORDレコード
ord-41c8ce546ecc4c64be692adc50335656
出典データセット
uspto-grants-2015_02
特許番号
US08946234B2

反応ノート

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