triethyloxidanium;tetrafluoroborate

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

Procedure: 3.20 g (16.83 mmol) of triethyloxonium tetrafluoroborate are added to a solution of 3.73 g (16.64 mmol) of N,N,N′,N′-tetramethyl-N″-ethylguanidinium bromide in 10 ml of dry dichloromethane. The reaction mixture is stirred at room temperature for 30 minutes. All volatile products are subsequently removed over the course of 30 minutes in a vacuum of 13.3 Pa and at 80° C. (oil-bath temperature), giving 3.84 g of N,N,N′,N′-tetramethyl-N″-ethylguanidinium tetrafluoroborate. The yield is approximately quantitative. All volatile products are subsequently removed over the course of 30 minutes in a vacuum of 13.3 Pa and at 80° C. (oil-bath temperature)

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

Procedure: 2.40 g (12.63 mmol) of triethyloxonium tetrafluoroborate are added to a solution of 2.45 g (12.62 mmol) of 1-ethyl-1-methylpyrrolidinium bromide in 10 ml of dry dichloromethane. The reaction mixture is stirred at room temperature for 30 minutes. All volatile products are subsequently removed over the course of 30 minutes in a vacuum of 13.3 Pa and at 80° C. (oil-bath temperature), giving 2.53 g of 1-ethyl-1-methylpyrrolidinium tetrafluoroborate. The yield is approximately quantitative. All volatile products are subsequently removed over the course of 30 minutes in a vacuum of 13.3 Pa and at 80° C. (oil-bath temperature)

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

Procedure: 2.48 g (13.04 mmol) of triethyloxonium tetrafluoroborate are added to a solution of 2.77 g (12.82 mmol) of 1-butylpyridinium bromide in 10 ml of dry dichloromethane. The reaction mixture is stirred at room temperature for 30 minutes. All volatile products are subsequently removed over the course of 30 minutes in a vacuum of 13.3 Pa and at 80° C. (oil-bath temperature), giving 2.82 g of 1-butylpyridinium tetrafluoroborate as liquid. The yield is approximately quantitative. All volatile products are subsequently removed over the course of 30 minutes in a vacuum of 13.3 Pa and at 80° C. (oil-bath temperature)

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

Procedure: 2.09 g (11.01 mmol) of triethyloxonium tetrafluoroborate are added to 2.21 g (10.90 mmol) of 1-hexyl-3-methylimidazolium chloride. The reaction mixture is stirred at room temperature for 30 minutes, and all volatile products are subsequently removed over the course of 30 minutes in a vacuum of 13.3 Pa and at 80° C. (temperature of the oil bath), giving 2.77 g of 1-hexyl-3-methylimidazolium tetrafluoroborate as liquid. The yield is approximately quantitative. all volatile products are subsequently removed over the course of 30 minutes in a vacuum of 13.3 Pa and at 80° C. (temperature of the oil bath),

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

Procedure: To a solution of 3-oxo-piperazine-1-carboxylic acid benzyl ester (2.0 g, 8.54 mmol, Maybridge) in dichloromethane (18 mL) at room temperature was added triethyloxonium tetrafluoroborate (4.1 g, 21.3 mmol). This mixture was allowed to stir for about 3 days then quenched by the addition of ice chips followed by saturated aqueous sodium bicarbonate until a neutral pH was obtained. The organic layer was separated and the aqueous layer was extracted with chloroform (3×). The combined organic extracts were washed with brine (1×), dried over sodium sulfate, and concentrated to give 2.11 g (95%) of the title compound of Example 259, Step A as a slightly yellow oil that was sufficiently pure to carry on to the next step. 1H NMR (CDCl3, 300 MHz) δ 7.43-6.97 (c, 5H), 5.17 (s, 2H), 4.10 (q, 2H), 3.98 (s, 2H), 3.60-3.40 (c, 4H), 1.27 (t, 3H); MS (APCI) 263 (MH+). then quenched by the addition of ice chips was obtained The organic layer was separated the aqueous layer was extracted with chloroform (3×) The combined organic extracts were washed with brine (1×) dried over sodium sulfate concentrated

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

Procedure: To N-[2-(5-methoxyindol-3-yl)ethyl]diacetamide (4) (35 mg) dissolved in dichloromethane (3 ml), at 0° C., is added Meerwein's reagent (0.15 mmol, 0.15 ml). The mixture is maintained at room temperature for 12 h. The solution is filtered. A red precipitate is obtained. The precipitate is dissolved in methanol (1 ml). After reacting for 15 min, the methanol is evaporated off and the ethyl acetate is extracted out. N-[2-(2-Acetyl-5-methoxyindol-3-yl)ethyl]acetamide (2) is thus obtained, Yield=75%. The solution is filtered A red precipitate is obtained the methanol is evaporated off the ethyl acetate is extracted out

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

Procedure: Analogously to Example 29b), 8.6 g (42 mmol) of 5-thiocarbamoyl-1-tetralone are treated with 8.8 g (44 mmol) of triethyloxonium tetrafluoroborate and 2.6 g (49 mmol) of ammonium chloride. There is thus obtained the title compound in the form of slightly pink-colored crystals, MS (FAB): (M+H)+ =189.

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

Procedure: To a solution of 10.5 ml of triethyloxonium tetrafluoroborate as a 1M solution in CH2Cl2, a solution of 1 g (7 mmol) of tetramethylazetidinethione in 3 ml of dry CH2Cl2 was added under an inert atmosphere. The mixture was stirred at room temperature for 1 hour and then at reflux for 1 hour. After cooling, it was added dropwise to 10 ml of a 50% K2CO3 solution at -10° C. After filtration, the organic phase was separated out and immediately dried over MgSO4. Filtration was followed by removal of the solvent under vacuum and the oily residue was subjected to flash silica chromatography (pet. ether: ethyl acetate; 8:2) to obtain the product as a colorless oil. at reflux for 1 hour After cooling After filtration the organic phase was separated out immediately dried over MgSO4 Filtration was followed by removal of the solvent under vacuum

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

Procedure: To a solution of 60 ml (1M) of triethyloxonium tetrafluoroborate in dichloromethane was added 5 g (0.039 mol) of tetramethylazetidinone in 10 ml of dry CH2Cl2 under an inert atmosphere. The reaction mixture was stirred for 1 hour at room temperature and then was refluxed for 1 hour. After cooling, the reaction mixture was added dropwise to 20 ml of a 50% K2CO3 solution at -10° C. and the mixture was diluted with 20 ml of CH2Cl2 and then filtered. The organic phase was separated out and immediately dried over MgSO4. After filtration, the solvent was stripped off under vacuum and the residue was distilled at 78° to 80° C./50 mmHg to obtain the product as a colorless oil. was refluxed for 1 hour After cooling filtered The organic phase was separated out immediately dried over MgSO4 After filtration the residue was distilled at 78° to 80° C./50 mmHg

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

Procedure: To a solution of 5,6-dimethoxysaccharin (0.8 g) in dichloromethane (100 ml) was added triethyloxonium tetrafluoroborate (3.5 ml, 1M soln in CH2Cl2) and the solution stirred at room temperature for 3 hrs. After extraction with aqueous sodium bicarbonate, the organic phase was dried and concentrated. Purification by column chromatography (silica, chloroform) gave the title compound (0.2 g). After extraction with aqueous sodium bicarbonate the organic phase was dried concentrated Purification by column chromatography (silica, chloroform)

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

Procedure: To a solution of 5,6-dimethoxysaccharin (0.8 g) in dichloromethane (100 ml) was added triethyloxonium tetrafluoroborate (3.5 ml, 1M soln in CH2Cl2) and the solution stirred at room temperature for 3 hrs. After extraction with aqueous sodium bicarbonate, the organic phase was dried and concentrated. Purification by column chromatography (silica, chloroform) gave the title compound (0.2 g). After extraction with aqueous sodium bicarbonate the organic phase was dried concentrated Purification by column chromatography (silica, chloroform)

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

Procedure: A solution of 151 g of triethyloxonium tetrafluoroborate in 3200 ml of methylene chloride was stirred under argon at room temperature for 3.5 hours after the addition of 106.6 g of 6-chloro-2,3-dihydro-1H-isoindole-1-one. The mixture was then treated within 40 minutes with 1.28 1 of saturated sodium hydrogen carbonate solution, the organic phase was separated and washed with 1.28 1 of water. After drying over sodium sulphate the organic phase was filtered and evaporated. The residue was taken up in 1.3 1 of diethyl ether, whereupon it was stirred at room temperature for about 30 minutes. After removing insoluble material by filtration the filtrate was evaporated. There was obtained 110.5 g of 1-ethoxy-6-chloro-3H-isoindole with a m.p. of 64°-66°. the organic phase was separated washed with 1.28 1 of water After drying over sodium sulphate the organic phase was filtered evaporated After removing insoluble material by filtration the filtrate was evaporated