Hydrochloric Acid → (2E)-3-[4-(4-fluorophenyl)-1-methyl-1H-pyrazol-5-yl]acrylic acid

HRID 30634ノート

反応式

HRID 30634 の反応式
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][N:13]([CH3:17])[C:14]=2[CH:15]=O)=[CH:6][CH:5]=1.C(OP([CH2:26][C:27]([O:29]CC)=[O:28])(OCC)=O)C.Cl>CN(C)C=O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][N:13]([CH3:17])[C:14]=2/[CH:15]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 85969110HCID 85969110、化合物

生成物 1

HCID 69209128(2E)-3-[4-(4-fluorophenyl)-1-methyl-1H-pyrazol-5-yl]acrylic acid収率 78.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% in oil, 60 mg) was added to a mixture of 4-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-carbaldehyde (168 mg), ethyl diethylphosphonoacetate (400 mg) and N,N-dimethylformamide (3 ml) at 0° C. and the mixture was stirred at room temperature for 15 min. The reaction mixture was poured into a 1N aqueous hydrochloric acid solution and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated and the residue was dissolved in a mixture of 6N hydrochloric acid (18 ml) and acetic acid (2 ml). The mixture was stirred for 1 hr. with heating under reflux. The reaction mixture was concentrated and poured into water. 1N Sodium hydroxide was added for neutralization. The precipitated solids were collected by filtration, washed with water, and dried to give (2E)-3-[4-(4-fluorophenyl)-1-methyl-1H-pyrazol-5-yl]acrylic acid (159 mg, 78%) as colorless crystals.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe ethyl acetate layer was concentrated
  3. dissolutionthe residue was dissolved in a mixture of 6N hydrochloric acid (18 ml) and acetic acid (2 ml)
  4. stirringThe mixture was stirred for 1 hr
  5. temperaturewith heating
  6. temperatureunder reflux
  7. concentrationThe reaction mixture was concentrated
  8. additionpoured into water
  9. addition1N Sodium hydroxide was added for neutralization
  10. filtrationThe precipitated solids were collected by filtration
  11. washwashed with water
  12. customdried

出典と根拠

ORDレコード
ord-a3d12dfc2d4d4a6f9702605c13b20559
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

反応ノート

読み込み中…