2-propan-2-ylthian-4-one

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

Procedure: 2-(1-methylethyl)tetrahydro-2H-thiopyran-4-one (1.185 g, 7.49 mmol) was dissolved in dry dichloromethane (DCM) (20 mL), cooled in an ice bath to ca 0° C., and stirred under argon. Trimethylsilyl trifluoromethanesulfonate (2.71 mL, 14.98 mmol) was added dropwise over 10 minutes, and dry DCM (5 mL) was used to wash in the last of the trimethylsilyltrifluoromethanesulfonate. To this mixture was added dropwise, a solution of ethyl 5-bromo-1H-indole-7-carboxylate (2.145 g, 8 mmol) in dry DCM (20 mL), and then an additional portion of dry DCM (5 mL) was used to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction. Triethylsilane (4.77 mL, 30.0 mmol) was added to the reaction in one portion. The resulting mixture was stirred 2 h at 0° C., and left stirring at 23° C. overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting biphasic mixture was extracted with DCM, dried (MgSO4) and the DCM was removed in vacuo to give the title compound as a dark yellow oil. cooled in an ice bath to ca 0° C. to wash in the last of the trimethylsilyltrifluoromethanesulfonate To this mixture was added dropwise to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction The resulting mixture was stirred 2 h at 0° C. left stirring at 23° C. overnight the resulting biphasic mixture was extracted with DCM dried (MgSO4) the DCM was removed in vacuo

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

Procedure: 7-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane was dissolved in acetic acid (50 mL) and 2 N aqueous hydrochloric acid (70 mL). After being stirred at room temperature for 15 h, the mixture was extracted with ether (300 mL), and the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL), and finally with water (2×50 mL). The dried (Na2SO4) solution was evaporated, and the residue purified by column chromatography on silica, giving 3.6 (22% over two steps) of the title compound. the mixture was extracted with ether (300 mL) the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL) The dried (Na2SO4) solution was evaporated the residue purified by column chromatography on silica

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

Procedure: 2-(1-methylethyl)tetrahydro-2H-thiopyran-4-one (1.185 g, 7.49 mmol) was dissolved in dry dichloromethane (DCM) (20 mL), cooled in an ice bath to ca 0° C., and stirred under argon. Trimethylsilyl trifluoromethanesulfonate (2.71 mL, 14.98 mmol) was added dropwise over 10 minutes, and dry DCM (5 mL) was used to wash in the last of the trimethylsilyltrifluoromethanesulfonate. To this mixture was added dropwise, a solution of ethyl 5-bromo-1H-indole-7-carboxylate (2.145 g, 8 mmol) in dry DCM (20 mL), and then an additional portion of dry DCM (5 mL) was used to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction. Triethylsilane (4.77 mL, 30.0 mmol) was added to the reaction in one portion. The resulting mixture was stirred 2 h at 0° C., and left stirring at 23° C. overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting biphasic mixture was extracted with DCM, dried (MgSO4) and the DCM was removed in vacuo to give the title compound as a dark yellow oil. cooled in an ice bath to ca 0° C. to wash in the last of the trimethylsilyltrifluoromethanesulfonate To this mixture was added dropwise to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction The resulting mixture was stirred 2 h at 0° C. left stirring at 23° C. overnight the resulting biphasic mixture was extracted with DCM dried (MgSO4) the DCM was removed in vacuo

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

Procedure: 7-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane was dissolved in acetic acid (50 mL) and 2 N aqueous hydrochloric acid (70 mL). After being stirred at room temperature for 15 h, the mixture was extracted with ether (300 mL), and the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL), and finally with water (2×50 mL). The dried (Na2SO4) solution was evaporated, and the residue purified by column chromatography on silica, giving 3.6 (22% over two steps) of the title compound. the mixture was extracted with ether (300 mL) the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL) The dried (Na2SO4) solution was evaporated the residue purified by column chromatography on silica

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

Procedure: 2-(1-methylethyl)tetrahydro-2H-thiopyran-4-one (1.185 g, 7.49 mmol) was dissolved in dry dichloromethane (DCM) (20 mL), cooled in an ice bath to ca 0° C., and stirred under argon. Trimethylsilyl trifluoromethanesulfonate (2.71 mL, 14.98 mmol) was added dropwise over 10 minutes, and dry DCM (5 mL) was used to wash in the last of the trimethylsilyltrifluoromethanesulfonate. To this mixture was added dropwise, a solution of ethyl 5-bromo-1H-indole-7-carboxylate (2.145 g, 8 mmol) in dry DCM (20 mL), and then an additional portion of dry DCM (5 mL) was used to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction. Triethylsilane (4.77 mL, 30.0 mmol) was added to the reaction in one portion. The resulting mixture was stirred 2 h at 0° C., and left stirring at 23° C. overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting biphasic mixture was extracted with DCM, dried (MgSO4) and the DCM was removed in vacuo to give the title compound as a dark yellow oil. cooled in an ice bath to ca 0° C. to wash in the last of the trimethylsilyltrifluoromethanesulfonate To this mixture was added dropwise to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction The resulting mixture was stirred 2 h at 0° C. left stirring at 23° C. overnight the resulting biphasic mixture was extracted with DCM dried (MgSO4) the DCM was removed in vacuo

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

Procedure: 7-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane was dissolved in acetic acid (50 mL) and 2 N aqueous hydrochloric acid (70 mL). After being stirred at room temperature for 15 h, the mixture was extracted with ether (300 mL), and the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL), and finally with water (2×50 mL). The dried (Na2SO4) solution was evaporated, and the residue purified by column chromatography on silica, giving 3.6 (22% over two steps) of the title compound. the mixture was extracted with ether (300 mL) the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL) The dried (Na2SO4) solution was evaporated the residue purified by column chromatography on silica

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

Procedure: 2-(1-methylethyl)tetrahydro-2H-thiopyran-4-one (1.185 g, 7.49 mmol) was dissolved in dry dichloromethane (DCM) (20 mL), cooled in an ice bath to ca 0° C., and stirred under argon. Trimethylsilyl trifluoromethanesulfonate (2.71 mL, 14.98 mmol) was added dropwise over 10 minutes, and dry DCM (5 mL) was used to wash in the last of the trimethylsilyltrifluoromethanesulfonate. To this mixture was added dropwise, a solution of ethyl 5-bromo-1H-indole-7-carboxylate (2.145 g, 8 mmol) in dry DCM (20 mL), and then an additional portion of dry DCM (5 mL) was used to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction. Triethylsilane (4.77 mL, 30.0 mmol) was added to the reaction in one portion. The resulting mixture was stirred 2 h at 0° C., and left stirring at 23° C. overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting biphasic mixture was extracted with DCM, dried (MgSO4) and the DCM was removed in vacuo to give the title compound as a dark yellow oil. cooled in an ice bath to ca 0° C. to wash in the last of the trimethylsilyltrifluoromethanesulfonate To this mixture was added dropwise to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction The resulting mixture was stirred 2 h at 0° C. left stirring at 23° C. overnight the resulting biphasic mixture was extracted with DCM dried (MgSO4) the DCM was removed in vacuo

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

Procedure: 7-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane was dissolved in acetic acid (50 mL) and 2 N aqueous hydrochloric acid (70 mL). After being stirred at room temperature for 15 h, the mixture was extracted with ether (300 mL), and the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL), and finally with water (2×50 mL). The dried (Na2SO4) solution was evaporated, and the residue purified by column chromatography on silica, giving 3.6 (22% over two steps) of the title compound. the mixture was extracted with ether (300 mL) the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL) The dried (Na2SO4) solution was evaporated the residue purified by column chromatography on silica

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

Procedure: 2-(1-methylethyl)tetrahydro-2H-thiopyran-4-one (1.185 g, 7.49 mmol) was dissolved in dry dichloromethane (DCM) (20 mL), cooled in an ice bath to ca 0° C., and stirred under argon. Trimethylsilyl trifluoromethanesulfonate (2.71 mL, 14.98 mmol) was added dropwise over 10 minutes, and dry DCM (5 mL) was used to wash in the last of the trimethylsilyltrifluoromethanesulfonate. To this mixture was added dropwise, a solution of ethyl 5-bromo-1H-indole-7-carboxylate (2.145 g, 8 mmol) in dry DCM (20 mL), and then an additional portion of dry DCM (5 mL) was used to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction. Triethylsilane (4.77 mL, 30.0 mmol) was added to the reaction in one portion. The resulting mixture was stirred 2 h at 0° C., and left stirring at 23° C. overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting biphasic mixture was extracted with DCM, dried (MgSO4) and the DCM was removed in vacuo to give the title compound as a dark yellow oil. cooled in an ice bath to ca 0° C. to wash in the last of the trimethylsilyltrifluoromethanesulfonate To this mixture was added dropwise to wash the last of ethyl 5-bromo-1H-indole-7-carboxylate into the reaction The resulting mixture was stirred 2 h at 0° C. left stirring at 23° C. overnight the resulting biphasic mixture was extracted with DCM dried (MgSO4) the DCM was removed in vacuo

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

Procedure: 7-(1-Methylethyl)-1,4-dioxa-8-thiaspiro[4.5]decane was dissolved in acetic acid (50 mL) and 2 N aqueous hydrochloric acid (70 mL). After being stirred at room temperature for 15 h, the mixture was extracted with ether (300 mL), and the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL), and finally with water (2×50 mL). The dried (Na2SO4) solution was evaporated, and the residue purified by column chromatography on silica, giving 3.6 (22% over two steps) of the title compound. the mixture was extracted with ether (300 mL) the ether extract washed with water (2×50 mL), 10% aqueous sodium hydroxide (3×50 mL) The dried (Na2SO4) solution was evaporated the residue purified by column chromatography on silica