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

HRID 1024356

반응식

HRID 1024356 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fc0630322fb142f182c4a87bbf48d283
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722887B2

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