Methylhydrazine → ethyl 2-(1,3,5-trimethyl-1H-pyrazol-4-yl)acetate

HRID 220457

반응식

HRID 220457 반응식
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH:6]([C:10](=O)[CH3:11])[C:7](=O)[CH3:8])[CH3:2].[CH3:14][NH:15][NH2:16]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:10]([CH3:11])=[N:16][N:15]([CH3:14])[C:7]=1[CH3:8])[CH3:2]

참가 물질

4

반응물 2

HCID 6061MethylhydrazineHCID 87820Ethyl 3-acetyl-4-oxopentanoate

생성물 1

HCID 16394807ethyl 2-(1,3,5-trimethyl-1H-pyrazol-4-yl)acetate수율 73.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Dissolve 3-acetyl-4-oxopentanoic acid ethyl ester (3.35 g, 19.5 mmol) in glacial acetic acid (20 mL) and add methylhydrazine (1.13 mL, 21.4 mmol) dropwise. Stir the resulting mixture at room temperature for 16 hr. Concentrate and partition the residue between ethyl acetate (100 mL) and saturated aqueous sodium bicarbonate solution (50 mL). Separate organic layer, dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 7:3 hexanes:ethyl acetate) to give (1,3,5-trimethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (2.8 g, 73%) as an oil. 1H NMR (CDCl3) δ 4.08 (q, 2H), 3.67 (s, 3H), 3.29 (s, 2H), 2.18 (s, 6H), 1.21 (t, 3H).

후처리

  1. concentrationConcentrate
  2. custompartition the residue between ethyl acetate (100 mL) and saturated aqueous sodium bicarbonate solution (50 mL)
  3. dry with materialSeparate organic layer, dry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 7:3 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-2d95a319eeab4885851635057c0e2465
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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