5,5,5-三氟戊腈

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 882 mg (18 mmole) of sodium cyanide and 9 mL of DMSO was heated in an oil bath at 80° C. for 10 minutes until most of the solid had dissolved. The mixture was then removed from the oil bath and treated with 2.87 g (15 mmole) of 4,4,4-trifluorobutyl bromide. The mixture was heated to 110° C. for about 30 minutes and then cooled to room temperature. The mixture was partitioned between H2O and ether, and the aqueous layer was extracted with an additonal 2 portions of ether. The combined organic fractions were washed successively with 2N HCl (twice), H2O (twice), and brine. The ether phase was dried over anhydrous Na2SO4, filtered, and concentrated to yield 1.99 g (97%) of the title compound as a colorless liquid, suitable for use without further purification; IR (neat) νCO 2260 cm-1. had dissolved The mixture was then removed from the oil bath The mixture was heated to 110° C. for about 30 minutes cooled to room temperature The mixture was partitioned between H2O and ether the aqueous layer was extracted with an additonal 2 portions of ether The combined organic fractions were washed successively with 2N HCl (twice), H2O (twice), and brine The ether phase was dried over anhydrous Na2SO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 882 mg (18 mmole) of sodium cyanide and 9 mL of DMSO was heated in an oil bath at 80° C. for 10 minutes until most of the solid had dissolved. The mixture was then removed from the oil bath and treated with 2.87 g (15 mmole) of 4,4,4-trifluorobutyl bromide. The mixture was heated to 110° C. for about 30 minutes and then cooled to room temperature. The mixture was partitioned between H2O and ether, and the aqueous layer was extracted with an additonal 2 portions of ether. The combined organic fractions were washed successively with 2N HCl (twice), H2O (twice), and brine. The ether phase was dried over anhydrous Na2SO4, filtered, and concentrated to yield 1.99 g (97%) of the title compound as a colorless liquid, suitable for use without further purification; IR (neat) νCO 2260 cm-1. had dissolved The mixture was then removed from the oil bath The mixture was heated to 110° C. for about 30 minutes cooled to room temperature The mixture was partitioned between H2O and ether the aqueous layer was extracted with an additonal 2 portions of ether The combined organic fractions were washed successively with 2N HCl (twice), H2O (twice), and brine The ether phase was dried over anhydrous Na2SO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 882 mg (18 mmole) of sodium cyanide and 9 mL of DMSO was heated in an oil bath at 80° C. for 10 minutes until most of the solid had dissolved. The mixture was then removed from the oil bath and treated with 2.87 g (15 mmole) of 4,4,4-trifluorobutyl bromide. The mixture was heated to 110° C. for about 30 minutes and then cooled to room temperature. The mixture was partitioned between H2O and ether, and the aqueous layer was extracted with an additonal 2 portions of ether. The combined organic fractions were washed successively with 2N HCl (twice), H2O (twice), and brine. The ether phase was dried over anhydrous Na2SO4, filtered, and concentrated to yield 1.99 g (97%) of the title compound as a colorless liquid, suitable for use without further purification; IR (neat) νCO 2260 cm-1. had dissolved The mixture was then removed from the oil bath The mixture was heated to 110° C. for about 30 minutes cooled to room temperature The mixture was partitioned between H2O and ether the aqueous layer was extracted with an additonal 2 portions of ether The combined organic fractions were washed successively with 2N HCl (twice), H2O (twice), and brine The ether phase was dried over anhydrous Na2SO4 filtered concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirring solution of 6.40 g (50.3 mM) 4,4,4-trifluorobutanol, prepared in Example 45d, and 7.71 ml (55.3 mM) triethylamine in 1.50 ml Et2O at 0° C. under N2, was added 4.28 ml (55.3 mM) methanesulfonyl chloride dropwise. A white precipitate formed and was stirred 60 minutes at 0° C. An equal volume of pentane was added and the reaction mixture was filtered through celite, followed by concentration on a rotary evaporator without heat. The crude mesylate was mixed with 8.19 g (126 mM) KCN and catalytic KI in 150 ml dimethysulfoxide at rt. The reaction mixture was then heated to 80° C. for 3 hours, turning deep orange and gelling. After cooling, the orange gel was poured into 100 ml of stirring H2O, extracted into Et2O, washed with saturated NaCl, dried over MgSO4, filtered and volatiles distilled. The crude liquid residue was 5.12 g (75%). A white precipitate formed the reaction mixture was filtered through celite followed by concentration on a rotary evaporator without heat The crude mesylate was mixed with 8.19 g (126 mM) KCN and catalytic KI in 150 ml dimethysulfoxide at rt The reaction mixture was then heated to 80° C. for 3 hours After cooling the orange gel was poured into 100 ml of stirring H2O extracted into Et2O washed with saturated NaCl dried over MgSO4 filtered volatiles distilled