Reaktion #704147

Reaktionsgleichung

tryptophol

acetonyl acetate

p-toluenesulfonic acid

water

→

1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanol

acetate

Lösungsmittel

ethyl acetate

benzene

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis refluxed for 11/2 hr
2. 2
   WaschenThe benzene solution is washed with 5% sodium bicarbonate, water
3. 3
   Sonstigedried
4. 4
   Sonstigeevaporated
5. 5
   Sonstigeto afford an oil

Vorschrift

A mixture of the starting material, tryptophol (32.2 g, 0.2 mole), acetonyl acetate (23.2 g, 0.2 mole) and 3.2 g of p-toluenesulfonic acid in 500 ml of benzene is refluxed for 11/2 hr. in the presence of a Dean-Stark water trap. The benzene solution is washed with 5% sodium bicarbonate, water, dried and evaporated to afford an oil. The oil is subjected to chromatography on a silica gel column using 10% ethyl acetate in benzene as eluent. The acetate, 1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanol, acetate is obtained as an oil, nmr(CDCl 3) δ1.52(S,3H), 2.08(S,3H), 4.35(2H).

Quelle