Reaktion #527043

Reaktionsgleichung

sodium hydroxide

triethylsilane

5,10-dihydro-8-tert-butylindeno[1,2-b]indole

water

→

cis-4b,5,9b,10-Tetrahydro-8-tert-butylindeno[1,2-b]indole

Lösungsmittel

trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe product was extracted into diethyl ether (2×5 cm3)
2. 2
   Waschenthe combined extracts were washed with water
3. 3
   Trocknendried (Na2SO4)
4. 4
   Sonstigeevaporated
5. 5
   Sonstigeto yield a pink solid
6. 6
   WaschenThis was washed with cold petroleum ether (60°-80° C.)
7. 7
   Sonstigecrystallised from petrol
8. 8
   Sonstigeto yield a colourless solid

Vorschrift

A solution of 5,10-dihydro-8-tert-butylindeno[1,2-b]indole (0.57 g, 2.2 mM) in trifluoroacetic acid (5 cm3) was stirred rapidly, and triethylsilane (0.7 cm3, 2 eq ) added in one portion. The reaction was stirred overnight, poured into water (10 cm3) and neutralised by the addition of sodium hydroxide. The product was extracted into diethyl ether (2×5 cm3), and the combined extracts were washed with water, dried (Na2SO4) and evaporated to yield a pink solid. This was washed with cold petroleum ether (60°-80° C.), and then crystallised from petrol to yield a colourless solid. Yield: 0.47 g, 81% M.p. 103°-105° C.; 1H NMR (CDCl3) δ: 7.4-6.9 (6H, m), 6.58 (1H, d, J=8 Hz), 5.25 (1H, d, J=8.5 Hz), 4.15 (2H, br.m), 3.5 (1H, dd, J=16.0 and 9 Hz), 3.2 (1H, d, J=16 Hz), 1.2 (9H, s).

Quelle