Ethyl Acetate → 2-(2-Trimethylsilanyl-ethoxymethyl)-2H-indazole-5-carbaldehyde

HRID 69193

Reaktionsgleichung

Reaktionsgleichung von HRID 69193
[N:1]1[NH:2][CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][C:6]([CH:10]=[O:11])=[CH:5]2.C1(C(N)C2CCCCC2)CCCCC1.Cl[CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32].CCOC(C)=O>C1COCC1>[CH3:32][Si:31]([CH3:34])([CH3:33])[CH2:30][CH2:29][O:28][CH2:27][N:2]1[CH:3]=[C:4]2[C:9]([CH:8]=[CH:7][C:6]([CH:10]=[O:11])=[CH:5]2)=[N:1]1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 178519387HCID 178519387, Verbindung

Produkt 1

HCID 866351152-(2-Trimethylsilanyl-ethoxymethyl)-2H-indazole-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2H-Indazole-5-carbaldehyde (Stage 150.5, 770 mg, 5.27 mmol) was dissolved in THF (54 mL) and dicyclohexylmethylamine (1.37 mL, 6.32 mmol) was added. After dropwise addition of (2-chloromethoxy-ethyl)-trimethyl-silane (1.21 mL, 6.32 mmol), the RM was stirred for 48 h at rt. It was then taken into EtOAc and washed successively with 0.5 M aqueous NaOH solution and brine. The organic layer was dried on Na2SO4 and evaporated and the residue purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=100:0->70:30) to afford white crystals of the title compound (tR 7.14 min (conditions 3), MH+=277).

Aufarbeitung

  1. washwashed successively with 0.5 M aqueous NaOH solution and brine
  2. customThe organic layer was dried on Na2SO4
  3. customevaporated
  4. customthe residue purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=100:0->70:30)

Quellen und Nachweise

ORD-Eintrag
ord-213deaad1c524c6183a358505892e2ea
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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