Potassium Hydroxide → 4-ethoxy-1-(4-fluorophenyl)-1H-pyrazole-3-carboxylic acid

HRID 1465185ノート

反応式

HRID 1465185 の反応式
[CH2:1]([O:3][C:4]1[C:5]([C:16]([O:18]CC)=[O:17])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:8]=1)[CH3:2].[OH-].[K+]>CCO.C(Cl)Cl.O>[CH2:1]([O:3][C:4]1[C:5]([C:16]([OH:18])=[O:17])=[N:6][N:7]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[CH:8]=1)[CH3:2]

参加物

6

反応物 2

HCID 14797Potassium HydroxideHCID 66611816Ethyl 4-ethoxy-1-(4-fluorophenyl)pyrazole-3-carboxylate

生成物 1

HCID 336766774-ethoxy-1-(4-fluorophenyl)-1H-pyrazole-3-carboxylic acid収率 93.4%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

D2 (38 mmol, 1.0 eq.) and aq. KOH-solution (3M, 190 mmol, 5.0 eq.) in EtOH (152 mL) were heated for 45 min at 50° C. The mixture was cooled to RT and diluted with DCM and water. The aq. phase was washed a second time with DCM. The aq. phase was acidified with aq. HCl-solution (1N) to pH=1 and extracted with EtOAc. The combined organic phase was washed with brine and dried over Na2SO4. Removal of the solvent yielded the product D3 as a brown solid (8.88 g, 93% over 2 steps). 1H NMR (400 MHz, d6-DMSO, 300K) δ 1.34 (t, J=7.0 Hz, 3H), 4.02 (q, J=7.0 Hz, 2H), 7.37 (dd, J=J=9.0 Hz, 2H), 7.87 (dd, J=9.0 Hz, J=4.6 Hz, 2H), 8.38 (s, 1H), 12.68 (br s, 1H). MS (ES) C12H11FN2O3 requires: 250. Found: 251 (M+H)+ and 273 (M+Na)+.

後処理

  1. washThe aq. phase was washed a second time with DCM
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent

出典と根拠

ORDレコード
ord-2e8ef89d5a6748dfaad9542f25ba378c
出典データセット
uspto-grants-2015_04
特許番号
US08999982B2

反応ノート

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