Diethyl Ether → 1-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,2-ethanedithiol

Participants

Reaction Conditions

Reaction Steps

Lithium aluminum hydride (0.622 g, 16.38 mmole) is added to 60 ml dry diethyl ether. To this slurry is added dropwise 4-(3,5-dimethoxy-4-methoxymethoxyphenyl)-1,3-dithiolane-2-thione (33) (3.40 g, 10.24 mmole) predissolved in 35 ml dry THF. The reaction is stirred under an N2 atmosphere until the solution becomes colorless (4 hours). The reaction is cooled to 0° C. and the excess hydride destroyed with H2O. The reaction mixture is acidified with 10% HCl and immediately extracted with diethyl ether. The organic layer is washed with H2O, dried over MgSO4, filtered and evaporated to a white solid (2.47 g, 84%). NMR: (CDCl3) 2.33,d,1H;2.90,m,1H;3.10,m,1H; 3.59,s,3H;3.85,s,6H;4.03,m,1H;5.10,s,2H;6.53,s,2H Melting Point: 84°-85° C. C,H,S analysis: (theoretical, actual) C (49.63,49.52); H (6.25,6.28); S (22.08,22.16).

Provenance & Evidence