2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 86651953, Verbindung

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Reaktionsgleichung

[Br:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>C(Cl)Cl.[OH-].[K+].CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[Br:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 4-bromo-1H-indazole-6-carbaldehyde (225 mg, 1 mmol) in CH2Cl2 (10 mL) and aqueous KOH (2 mL, 50% wt) at 0° C. was added TBAB (3 mg, 0.01 mmol) and SEMCl (200 mg, 1.2 mmol). The mixture was stirred at 0° C. for 4 h, warmed to rt and extracted with ethyl acetate (100 mL). The organic phase was washed with water (2×10 mL) and brine (10 mL), dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (1:1 EtOAc/Hex) to give the title compound as a pale yellow solid (280 mg, 82%). 1H NMR (400 MHz, CD3OD) δ 10.02 (s, 1H), 8.21-8.19 (m, 2H), 7.80 (s, 1H), 5.78 (s, 2H), 3.70-3.65 (m, 2H), 0.95-0.92 (m, 2H), −0.05 (s, 9H).

Aufarbeitung

temperaturewarmed to rt
extractionextracted with ethyl acetate (100 mL)
washThe organic phase was washed with water (2×10 mL) and brine (10 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography (1:1 EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag: ord-9eb12490dad24e6580fa33006e17dcd0
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08765748B2

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