Methylhydrazine → ethyl 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)propanoate

HRID 220462ノート

反応式

HRID 220462 の反応式
[C:1]([CH:4]([C:12](=O)[CH3:13])[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH3:2].[CH3:15][NH:16][NH2:17]>C(O)(=O)C>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][C:4]1[C:12]([CH3:13])=[N:17][N:16]([CH3:15])[C:1]=1[CH3:2])[CH3:11]

参加物

4

反応物 2

HCID 6061MethylhydrazineHCID 2733934Hexanoic acid, 4-acetyl-5-oxo-, ethyl ester

生成物 1

HCID 16394809ethyl 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)propanoate収率 93%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Dissolve ethyl 4-acetyl-5-oxohexanoate (2.00 g, 9.99 mmol) in acetic acid (21 mL). Add methyl hydrazine (589 μL, 10.99 mmol) and stir at room temperature for 18 hr. Concentrate and dissolve residue in ethyl acetate. Wash ethyl acetate layer with saturated aqueous sodium bicarbonate solution. Extract aqueous layer twice with ethyl acetate, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 100% ethyl acetate:hexanes) to give 3-(1,3,5-trimethyl-1H-pyrazol-4-yl)-propionic acid ethyl ester (1.95 g, 93%). MS (ES): m/z=211 [M+H]+.

後処理

  1. concentrationConcentrate
  2. dissolutiondissolve residue in ethyl acetate
  3. dry with materialExtract aqueous layer twice with ethyl acetate, dry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 0:100 to 100% ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-000c6f90b8f246098496a859eabe70f4
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

反応ノート

読み込み中…