Reaktion #8411

Reaktionsgleichung

4-Chloroindole

t-BuOK

Tert-butyldimethylchlorosilane

→

title compound

Ausbeute 78.0%

N-tert-Butyl-trimethylsilyl-4-chloroindole

Ausbeute 78.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 30 minutes the reaction was quenched with water (20 ml) and pH
2. 2
   Extraktionextracted with ethyl acetate (3×50 mL)
3. 3
   TrocknenThe organic phases were dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   SonstigeThe residue was triturated
6. 6
   Sonstigecrystallized from heptane

Vorschrift

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).

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