Diethyl Ether → 4-methyl-5-phenyl-4,5-dihydro-1H-pyrazole

HRID 12497

反応式

HRID 12497 の反応式
O.[NH2:2][NH2:3].C(OCC)C.[CH3:9][C:10](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:11]=O>O>[CH3:9][CH:10]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:3][N:2]=[CH:11]1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 75572-Methylcinnamic aldehydeHCID 24654Hydrazine hydrate (1:1)

生成物 1

HCID 593393074-methyl-5-phenyl-4,5-dihydro-1H-pyrazole

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5.22 ml (1 equiv.) hydrazine hydrate was added to 100 mL diethylether. The emulsion was cooled with an ice bath. 15.0 mL 2-Methyl-3-phenyl-propenal was added dropwise, and the mixture was stirred overnight at room temperature. H2O was added, the organic layer was separated and the aqueous layer was extracted with diethylether. The combined organic layers were dried over Na2SO4, filtrated and concentrated in vacuo. Vacuum distillation yielded 5.9 g of desired product (mixture of diastereomeric pairs) as a clear fluid (76-82° C., 0.2-0.3 mbar). 1H NMR (400 MHz, CDCl3) of first diastereomeric pair; δ 0.71 (d, J=7 Hz), 3H), 3.20-3.31 (m, 1H), 4.77 (d, J=10 Hz, 1H), 6.73 (br s, 1H), 7.23-7.42 (m, 5H), 8.55-8.60 (m, 2H). 1H NMR (400 MHz, CDCl3) of second diastereomeric pair: δ 1.24 (d, J=7 Hz), 3H), 2.90-3.11 (m, 1H), 4.22 (d, J=11 Hz, 1H), 6.71 (br s, 1H), 7.23-7.42 (m, 5H), 8.55-8.60 (m, 2H).

後処理

  1. temperatureThe emulsion was cooled with an ice bath
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with diethylether
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. distillationVacuum distillation

出典と根拠

ORDレコード
ord-a7d533dfc1c64b57a8781969f0672fcd
出典データセット
uspto-grants-2010_06
特許番号
US07728018B2

関連ノート

読み込み中…