Reaktion #577963

Reaktionsgleichung

6-methoxyindole

EtOAc

3,4,5-trimethoxybenzoyl chloride CH2Cl2

AlCl3

→

Compound 1

Ausbeute 72.0%

(6-Methoxy-1H-indol-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone

Ausbeute 72.0%

Lösungsmittel

CH2Cl2

EtMgBr

n-hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added over 10 min at room temperature
2. 2
   workup.STIRRINGThe reaction mixture continued stirring for another 1 hr
3. 3
   SonstigeThe reaction was quenched with H2O (10 ml)
4. 4
   Extraktionextracted with CH2Cl2 (10 mL×3)
5. 5
   TrocknenThe combined extracts was dried by MgSO4
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give a brown oil which
8. 8
   Sonstigewas chromatographed (silica gel; EtOAc: n-hexane=1:1)

Vorschrift

To a mixture of 6-methoxyindole (0.3 g, 2.03 mmol) and anhydrous ZnCl2 (0.56 g, 4.07 mmol) in CH2Cl2 (10 mL), EtMgBr (0.9 ml, 3 M) was added over 10 min at room temperature. The obtained suspension was stirred for 1 hr. To the suspension, the solution of 3,4,5-trimethoxybenzoyl chloride/CH2Cl2 (10 ml) was added dropwisely during 5 min for a coupling reaction. The reaction mixture continued stirring for another 1 hr and AlCl3 (0.27 g, 2.03 mmol) was added. The resultant thick mixture was vigorously stirred for 5 hr while monitoring by TLC (EtOAc: n-hexane=1:1). The reaction was quenched with H2O (10 ml) and extracted with CH2Cl2 (10 mL×3). The combined extracts was dried by MgSO4, and evaporated to give a brown oil which was chromatographed (silica gel; EtOAc: n-hexane=1:1) to afford Compound 1 (0.5 g, 72%) as a white solid.

Quelle