Reaktion #981387

Reaktionsgleichung

methyl 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylate

methanethiol

thionyl chloride

potassium tert-butoxide

thionyl chloride

→

title product

Ausbeute 84.0%

Methyl 6,11-dihydrodibenz[b,e]oxepin-2-carboxylate

Ausbeute 84.0%

Lösungsmittel

water

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturReflux 4.4 gm
2. 2
   workup.ADDITIONAdd the mixture to a solution of 3.84 gm
3. 3
   Extraktionextract with ether
4. 4
   SonstigeEvaporate to dryness and chromatograph over silica gel
5. 5
   Wascheneluting with toluene
6. 6
   SonstigeEvaporate to dryness

Vorschrift

Reflux 4.4 gm. of methyl 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-carboxylate with 20 ml. of thionyl chloride for 10 minutes. Evaporate excess thionyl chloride and dissolve the residue in 30 ml. of dimethylformamide. Add the mixture to a solution of 3.84 gm. of potassium tert-butoxide in 75 ml. of dimethylformamide saturated with methanethiol. Stir at room temperature for 24 hours, dilute with water and extract with ether. Evaporate to dryness and chromatograph over silica gel, eluting with toluene. Evaporate to dryness to obtain the title product as an oil (yield 3.03 gm., 84%).

Quelle