Toluene → Methyl 2-(4-acetyl-5-methyl-1H-pyrazol-1-yl)acetate

HRID 2425547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2425547
[C:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]([OH:13])=[O:12])[C:8]=1[CH3:9])(=[O:3])[CH3:2].[C:14]1(C)C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C.CCOCC>CO>[C:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:8]=1[CH3:9])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 632769652-(4-acetyl-5-methyl-1H-pyrazol-1-yl)acetic acid

Produkt 1

HCID 67181907Methyl 2-(4-acetyl-5-methyl-1H-pyrazol-1-yl)acetateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-acetyl-5-methyl-1H-pyrazol-1-yl)acetic acid (1.17 g, 6.42 mmol, as a mixture of regioisomers from the previous step) in MeOH (8.8 ml)-Toluene (30.6 ml) was added a 2 M solution of (trimethylsilyl)diazomethane in ether (4.8 ml, 9.6 mmol) dropwise at 0° C. The resulting solution was allowed to warm to rt and stirred for 120 min. The reaction was quenched by addition of AcOH (3 ml) and the solvent was concentrated in vacuo. The crude product was purified by silica gel column chromatography (CH2Cl2:MeOH=30:1) to give the desired product along with a mixture of regioisomers (>99% yield). 1H NMR (270 MHz, CDCl3) δ 2.45 (3H, s), 2.53 (3H, s), 3.79 (3H, s), 4.90 (2H, s), 7.88 (1H, s).

Aufarbeitung

  1. customThe reaction was quenched by addition of AcOH (3 ml)
  2. concentrationthe solvent was concentrated in vacuo
  3. customThe crude product was purified by silica gel column chromatography (CH2Cl2:MeOH=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-482840abe9c74daa8b9da94f887c52c0
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964732B2

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