3-Phenylprop-2-Enal → 5-Phenyl-4,5-dihydro-1H-pyrazole

HRID 12495

反応式

HRID 12495 の反応式
O.[NH2:2][NH2:3].[CH:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CC(O)(C)C>[C:7]1([CH:6]2[NH:3][N:2]=[CH:4][CH2:5]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

4

反応物 2

HCID 3073-Phenylprop-2-EnalHCID 24654Hydrazine hydrate (1:1)

生成物 1

HCID 1208415-Phenyl-4,5-dihydro-1H-pyrazole

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

Under N2 atmosphere, hydrazine hydrate (9.2 mL) was added to a solution of cinnamaldehyde (10.0 g) in t-BuOH (20 mL). The mixture was refluxed overnight, followed by concentration under reduced pressure. Water was added to the residue, and the aqueous phase was extracted twice with DCM. The combined organic layers were washed with water, dried over Na2SO4 and concentrated under reduced pressure. This gave 10.46 g of a yellow oil containing 85% of the desired product, which was used in subsequent steps without further purification. 1H NMR (200 MHz, CDCl3) δ 2.61-2.80 (m, 1H), 3.04-3.23 (m, 1H), 4.72 (dd, J=8 and 10 Hz, 1H), 5.60-6.10 (br s, 1H), 6.77-6.87 (m, 1H), 7.18-7.47 (m, 5H).

後処理

  1. temperatureThe mixture was refluxed overnight
  2. concentrationfollowed by concentration under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe aqueous phase was extracted twice with DCM
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. additionThis gave 10.46 g of a yellow oil containing 85% of the desired product, which
  9. customwas used in subsequent steps without further purification

出典と根拠

ORDレコード
ord-cc69153d0baf4ca4ad6a0b45e3ed5cb5
出典データセット
uspto-grants-2010_06
特許番号
US07728018B2

関連ノート

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