Reaktion #528797

ord-6755dbaba82848aeb24e2bbea8fa9082

Reaktionsgleichung

OCCc1c[nH]c2ccccc12
tryptophol
CC(C)=O
acetone
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
CC(C)=O
acetone
→
CC1(C)OCCc2c1[nH]c1ccccc21
1,1-DIMETHYL-1,3,4,9-TETRAHYDROPYRANO-[3,4-b]INDOLE

Edukte

OCCc1c[nH]c2ccccc12
tryptophol
CC(C)=O
acetone
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
—
ketone
Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulfonic acid
CC(C)=O
acetone

Reagenzien

Keine

Lösungsmittel

c1ccccc1
benzene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturto reflux for 1 hr

Vorschrift

A solution of tryptophol (8 g, 0.05M), acetone (5 g) and p-toluenesulfonic acid (100 mg) in 100 ml benzene containing hydrated alkali-aluminum silicate (Molecular Sieves No. 4) is heated to reflux for 1 hr. More p-toluenesulfonic acid (100 mg) and the ketone, acetone (3 g), is added and the reflux contained for a further 1.5 hr.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04041169uspto-grants-1977_08