1-(3,4-dihydroxyphenyl)-2-methylsulfanylethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of α-methylthioacetophenone, starting with a stirred solution of 4-(2-chloroacetyl)pyrocatechol (18.6 g) in methanol (200 cc). Sodium methanethiolate (7 g) is added in the course of 15 minutes at a temperature in the region of 20° C., and the mixture is left with stirring for 3 hours at the same temperature. 4-[2-(Methylthio)acetyl]pyrocatechol (14.5 g), m.p. 107° C., is thereby obtained. the mixture is left

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino-2,4-hexadienoate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (11.4 g), a 2M ethanolic solution of sodium ethylate (60 cc) and 4-[2-(methylthio)acetyl]pyrocatechol (7.9 g) in ethanol (60 cc). After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent, ethyl 6-(3,4-dihydroxyphenyl)-2-dimethylamino-5-methylthio-6-oxo-2,4-hexadienoate (2.4 g), m.p. 144° C., is obtained. After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino-2,4-hexadienoate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (11.4 g), a 2M ethanolic solution of sodium ethylate (60 cc) and 4-[2-(methylthio)acetyl]pyrocatechol (7.9 g) in ethanol (60 cc). After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent, ethyl 6-(3,4-dihydroxyphenyl)-2-dimethylamino-5-methylthio-6-oxo-2,4-hexadienoate (2.4 g), m.p. 144° C., is obtained. After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of α-methylthioacetophenone, starting with a stirred solution of 4-(2-chloroacetyl)pyrocatechol (18.6 g) in methanol (200 cc). Sodium methanethiolate (7 g) is added in the course of 15 minutes at a temperature in the region of 20° C., and the mixture is left with stirring for 3 hours at the same temperature. 4-[2-(Methylthio)acetyl]pyrocatechol (14.5 g), m.p. 107° C., is thereby obtained. the mixture is left

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of α-methylthioacetophenone, starting with a stirred solution of 4-(2-chloroacetyl)pyrocatechol (18.6 g) in methanol (200 cc). Sodium methanethiolate (7 g) is added in the course of 15 minutes at a temperature in the region of 20° C., and the mixture is left with stirring for 3 hours at the same temperature. 4-[2-(Methylthio)acetyl]pyrocatechol (14.5 g), m.p. 107° C., is thereby obtained. the mixture is left

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino-2,4-hexadienoate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (11.4 g), a 2M ethanolic solution of sodium ethylate (60 cc) and 4-[2-(methylthio)acetyl]pyrocatechol (7.9 g) in ethanol (60 cc). After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent, ethyl 6-(3,4-dihydroxyphenyl)-2-dimethylamino-5-methylthio-6-oxo-2,4-hexadienoate (2.4 g), m.p. 144° C., is obtained. After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of α-methylthioacetophenone, starting with a stirred solution of 4-(2-chloroacetyl)pyrocatechol (18.6 g) in methanol (200 cc). Sodium methanethiolate (7 g) is added in the course of 15 minutes at a temperature in the region of 20° C., and the mixture is left with stirring for 3 hours at the same temperature. 4-[2-(Methylthio)acetyl]pyrocatechol (14.5 g), m.p. 107° C., is thereby obtained. the mixture is left

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino-2,4-hexadienoate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (11.4 g), a 2M ethanolic solution of sodium ethylate (60 cc) and 4-[2-(methylthio)acetyl]pyrocatechol (7.9 g) in ethanol (60 cc). After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent, ethyl 6-(3,4-dihydroxyphenyl)-2-dimethylamino-5-methylthio-6-oxo-2,4-hexadienoate (2.4 g), m.p. 144° C., is obtained. After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of α-methylthioacetophenone, starting with a stirred solution of 4-(2-chloroacetyl)pyrocatechol (18.6 g) in methanol (200 cc). Sodium methanethiolate (7 g) is added in the course of 15 minutes at a temperature in the region of 20° C., and the mixture is left with stirring for 3 hours at the same temperature. 4-[2-(Methylthio)acetyl]pyrocatechol (14.5 g), m.p. 107° C., is thereby obtained. the mixture is left

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure is as in Example 4 for the preparation of ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino-2,4-hexadienoate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (11.4 g), a 2M ethanolic solution of sodium ethylate (60 cc) and 4-[2-(methylthio)acetyl]pyrocatechol (7.9 g) in ethanol (60 cc). After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent, ethyl 6-(3,4-dihydroxyphenyl)-2-dimethylamino-5-methylthio-6-oxo-2,4-hexadienoate (2.4 g), m.p. 144° C., is obtained. After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent