Methanol → Ethyl 4-ethoxy-1-(4-fluorophenyl)pyrazole-3-carboxylate

HRID 1465184ノート

反応式

HRID 1465184 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([OH:13])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:26][CH3:27].CO>CN(C=O)C.C(Cl)Cl>[CH2:26]([O:13][C:11]1[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:12]=1)[CH3:27]

参加物

7

反応物 4

HCID 887MethanolHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 730292Ethyl 1-(4-fluorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylate

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of D1 (9.6 g, 38 mmol, 1.0 eq.) and K2CO3 (6.8 g, 50 mmol, 1.3 eq.) in dry DMF (100 mL) was added at RT iodoethane (4.0 mL, 7.8 g, 50 mmol, 1.3 eq.). After stirring for 72 h at RT the mixture was cooled to 0° C. MeOH (5 mL) was added, the mixture was diluted with DCM (200 mL) and washed with water and phosphate buffer. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the product D2 as a brown solid which was used without further purification in the subsequent step. MS (ES) C14H15FN2O3 requires: 278. Found: 279 (M+H)+.

後処理

  1. temperaturewas cooled to 0° C
  2. washwashed with water and phosphate buffer
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-57e6532bcfd64476957ad73a83a64889
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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