Methyl iodide → 7-[3-(2-Methoxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester

HRID 1443677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443677
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])=[N:14]1)[CH3:4].I[CH3:27]>C1COCC1>[CH2:3]([O:5][C:6](=[O:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:27])=[N:14]1)[CH3:4]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1362065297-[3-(2-Hydroxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester

Produkt 1

HCID 684889907-[3-(2-Methoxyphenyl)pyrazol-1-yl]heptanoic acid ethyl esterAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add sodium hydride (900 mg, 18 mmol, 60% suspension in mineral oil) to a suspension of 7-[3-(2-hydroxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester (4.73 g, 15 mmol) and iodomethane (1.1 mL, 18 mmol) in THF (70 mL) at 0° C. under nitrogen and warm the mixture to room temperature to stir for 12 hours. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (150 mL), wash with water (100 mL), and dry over sodium sulfate. Remove the solvent under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (9:1), to provide 7-[3-(2-Methoxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester (3.75 g, 76%).

Aufarbeitung

  1. customRemove the solvent under reduced pressure
  2. additiondilute the residue with ethyl acetate (150 mL)
  3. washwash with water (100 mL)
  4. dry with materialdry over sodium sulfate
  5. customRemove the solvent under reduced pressure
  6. custompurify the residue by flash column chromatography on silica gel
  7. washeluting with hexanes/ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-66f603671d2d47fb94cb4a7c4f0e095f
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662771B2

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