methyl 3-cyclopropylprop-2-ynoate

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

Procedure: 1.45 g (3.00 mmol, purity 98%) of 1-amino-4-methyl-2-[(2,3,6-trifluorobenzyl)oxy]pyridinium 2,4,6-trimethylbenzenesulphonate from Example 155A were dissolved in 9.7 ml of DMF and admixed with 670 mg (5.40 mmol) of methyl 3-cyclopropylprop-2-ynoate. 747 mg (5.40 mmol) of potassium carbonate was added and the mixture was stirred at RT for 3 h. Subsequently, the mixture was poured onto 73 ml of water and stirred briefly, and the precipitated solids were filtered off, washed with water and dried. 462 mg of the title compound were obtained (33% of theory; 85% purity). stirred briefly the precipitated solids were filtered off washed with water dried

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

Procedure: 1.0 g (2.22 mmol) of 1-amino-2-[(2,6-difluorobenzyl)oxy]-4-methylpyridinium 2,4,6-trimethylbenzenesulphonate from Example 2A were dissolved in 7.2 ml of DMF, and 496 mg (4.00 mmol) of methyl 3-cyclopropylprop-2-ynoate were added. 552 mg (4.00 mmol) of potassium carbonate were added and the mixture was stirred at RT for 3 h. Subsequently, the mixture was poured onto 50 ml of water and stirred briefly, and the precipitated solids were filtered off, washed with water and dried. 384 mg of the title compound were obtained (46% of theory). stirred briefly the precipitated solids were filtered off washed with water dried

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of cyclopropyl acetylene (10.0 g, 148 mmol) in 50 mL of ethyl ether at −78° C. under argon was added methyllithiium (1.4 M in ethyl ether, 107 mL, 150 mmol). This solution was stirred at −78° C. for 1 h. Methyl chloroformate (12.0 mL, 154 mmol) was added. The reaction mixture was warmed to room temperature in 2 h and was quenched with water. The organic layer was separated. The aqueous layer was extracted with ethyl ether (50 mL×3). The combined organic layer was dried over sodium sulfate and evaporated to give cyclopropyl-propynoic acid methyl ester as a yellow oil (13.25 g, 72%). The reaction mixture was warmed to room temperature in 2 h was quenched with water The organic layer was separated The aqueous layer was extracted with ethyl ether (50 mL×3) The combined organic layer was dried over sodium sulfate evaporated