Diisopropylethylamine → Ethyl 3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carboxylate

HRID 42272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42272
[I:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl>ClCCl.[Cl-].[Na+].O>[I:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[N:3]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178469927HCID 178469927, Verbindung

Produkt 1

HCID 67505121Ethyl 3-iodo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of EXAMPLE 59A (1.3 g, 5 mmole) and diisopropyl-ethyl amine (1.3 mL, 7.5 mmole) in dichloromethane (20 mL) at ambient temperature was added 2-(trimethylsilyl)ethoxymethyl chloride (1.25 g, 7.5 mmole) dropwise. The solution was stirred overnight. Brine (20 mL) was added and the mixture was extracted with ethyl acetate. The mixture was dried with magnesium sulfate, filtered and concentrated. The residue was purified on a silica gel column eluting with 25% ethyl acetate in hexane. The two regioisomers were isolated as a mixture. MS (DCI) m/e 397 (M+H)+.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe mixture was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column
  6. washeluting with 25% ethyl acetate in hexane
  7. customThe two regioisomers were isolated as a mixture

Quellen und Nachweise

ORD-Eintrag
ord-34c59c89e1c0457e990b2b04352e16d5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536180B2

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