tert-Butyldimethylsilyl chloride → HCID 22015415, Verbindung

HRID 8315

Reaktionsgleichung

[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:11][C:12]([O-])([CH3:14])[CH3:13].[K+].[C:17]([Si:21]([CH3:24])([CH3:23])Cl)(C)(C)C>C1COCC1>[C:12]([N:6]1[C:7]2[C:3](=[C:2]([Cl:1])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[C:5]1[Si:21]([CH3:24])([CH3:23])[CH3:17])([CH3:14])([CH3:13])[CH3:11]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

4-Chloroindole (131.1 g, 0.871 mol) was dissolved in dry THF (0.5 L). The solution was chilled to 0° C. (ice bath, stirring). t-BuOK (97.6 g, 0.871 mol) was added in one portion and the stirring was continued for additional 5 minutes. Tert-butyldimethylchlorosilane (131 .3 g, 0.871 mol) was added portionwise over 10 min with a good stirring. The reaction is exothermic. After 30 minutes the reaction was quenched with water (20 ml) and pH was adjusted to 8–9 and extracted with ethyl acetate (3×50 mL). The organic phases were dried (MgSO4), filtered and the volatiles were eliminate by vacuum. The residue was triturated and crystallized from heptane to yield 181 g (78%) of the title compound. 1H NMR (CDCl3) δ 7.45 (dd, J=7.9 Hz, J==0.8 Hz, 1 H), 7.25 (d, J=3.0 Hz, 1 H), 7.18–7.07 (m, 2 H), 6.77 (d, 1 H), 0.96 (s, 9 H), 0.62 (s, 6 H); 13C NMR (CDCl3) 141.8; 131.7; 130.3; 125.9; 122.0; 119.7; 112.5; 103.5; 26.3; 19.5; −3.9; MS (ESI) 266.1 (M+H).

Aufarbeitung

customAfter 30 minutes the reaction was quenched with water (20 ml) and pH
extractionextracted with ethyl acetate (3×50 mL)
dry with materialThe organic phases were dried (MgSO4)
filtrationfiltered
customThe residue was triturated
customcrystallized from heptane

Quellen und Nachweise

ORD-Eintrag: ord-dd1e98bf82a04769a645501fc6827542
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07087750B2

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