decan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 2.7 g (17.0 mmol) of 2-decanol were added dropwise at 50° C. to a suspension of 650 mg (21.6 mmol) of sodium hydride (80% suspension in oil) in 60 ml of dry dimethylformamide, and the mixture was stirred until the evolution of hydrogen had ceased. The mixture was cooled to room temperature and 3.0 g (15.9 mmol) of 4-chloro-5-methoxy-6-ethoxypyrimidine (preparation analogously to Example C) were added in portions. After 30 minutes, the reaction temperature was increased to 50° C., and stirring was continued for 12 hours. The reaction mixture was poured into saturated ammonium chloride solution and subsequently extracted with diethyl ether. The combined organic phase was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel using n-heptane/ethyl acetate (4:1). 1.4 g (28% of theory) of 4-(2-decyloxy)-5-methoxy-6-ethoxypyrimidine were obtained in the form of a yellow oil. were added in portions the reaction temperature was increased to 50° C. was continued for 12 hours subsequently extracted with diethyl ether The combined organic phase was washed with water dried over magnesium sulfate concentrated in vacuo The residue was chromatographed on silica gel

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

Procedure: To a solution of 2-decanol (5.0 ml, 26.0 mmol) in dry CH2Cl2 (52 ml) under an N2 atmosphere was added diisopropylethylamine (5.6 ml, 32.1 mmol). The reaction flask was immersed in an ice/water bath. After stirring for 10 minutes, methanesulfonyl chloride (2.8 ml, 36.1 mmol) was added via syringe over a period of 10 minutes. After stirring for 3 hrs, the reaction was diluted with cold CH2Cl2 (200 ml) and poured into cold 5% aqueous HCl (100 ml). The layers were separated and the organic phase washed with cold 5% aqueous HCl (50 ml) followed by brine (2×50 ml). The CH2Cl2 layer was dried (Na2SO4), filtered and evaporated in vacuo at 25° C. The resulting light yellow oil was pumped under reduced pressure for 2 hrs to provide 2-methanesulfonyloxydecane (6.5 g, 93.5%) as a light yellow oil. The reaction flask was immersed in an ice/water bath After stirring for 3 hrs The layers were separated the organic phase washed with cold 5% aqueous HCl (50 ml) The CH2Cl2 layer was dried (Na2SO4) filtered evaporated in vacuo at 25° C The resulting light yellow oil was pumped under reduced pressure for 2 hrs

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

Procedure: To a solution of 2-decanol (5.0 ml, 26.0 mmol) in dry CH2Cl2 (52 ml) under an N2 atmosphere was added diisopropylethylamine (5.6 ml, 32.1 mmol). The reaction flask was immersed in an ice/water bath. After stirring for 10 minutes, methanesulfonyl chloride (2.8 ml, 36.1 mmol) was added via syringe over a period of 10 minutes. After stirring for 3 hrs, the reaction was diluted with cold CH2Cl2 (200 ml) and poured into cold 5% aqueous HCl (100 ml). The layers were separated and the organic phase washed with cold 5% aqueous HCl (50 ml) followed by brine (2×50 ml). The CH2Cl2 layer was dried (Na2SO4), filtered and evaporated in vacuo at 25° C. The resulting light yellow oil was pumped under reduced pressure for 2 hrs to provide 2-methanesulfonyloxydecane (6.5 g, 93.5%) as a light yellow oil. The reaction flask was immersed in an ice/water bath After stirring for 3 hrs The layers were separated the organic phase washed with cold 5% aqueous HCl (50 ml) The CH2Cl2 layer was dried (Na2SO4) filtered evaporated in vacuo at 25° C The resulting light yellow oil was pumped under reduced pressure for 2 hrs

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

Procedure: 3-decanol and 4-decanol (1.10 mmol); 2-decanone (1.73 mmol); 3-decanone and 4-decanone (1.41 mmol).

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

Procedure: 3-decanol and 4-decanol (1.10 mmol); 2-decanone (1.73 mmol); 3-decanone and 4-decanone (1.41 mmol).

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

Procedure: 2.7 g (17.0 mmol) of 2-decanol were added dropwise at 50° C. to a suspension of 650 mg (21.6 mmol) of sodium hydride (80% suspension in oil) in 60 ml of dry dimethylformamide, and the mixture was stirred until the evolution of hydrogen had ceased. The mixture was cooled to room temperature and 3.0 g (15.9 mmol) of 4-chloro-5-methoxy-6-ethoxypyrimidine (preparation analogously to Example C) were added in portions. After 30 minutes, the reaction temperature was increased to 50° C., and stirring was continued for 12 hours. The reaction mixture was poured into saturated ammonium chloride solution and subsequently extracted with diethyl ether. The combined organic phase was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel using n-heptane/ethyl acetate (4:1). 1.4 g (28% of theory) of 4-(2-decyloxy)-5-methoxy-6-ethoxypyrimidine were obtained in the form of a yellow oil. were added in portions the reaction temperature was increased to 50° C. was continued for 12 hours subsequently extracted with diethyl ether The combined organic phase was washed with water dried over magnesium sulfate concentrated in vacuo The residue was chromatographed on silica gel

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

Procedure: To a solution of 2-decanol (5.0 ml, 26.0 mmol) in dry CH2Cl2 (52 ml) under an N2 atmosphere was added diisopropylethylamine (5.6 ml, 32.1 mmol). The reaction flask was immersed in an ice/water bath. After stirring for 10 minutes, methanesulfonyl chloride (2.8 ml, 36.1 mmol) was added via syringe over a period of 10 minutes. After stirring for 3 hrs, the reaction was diluted with cold CH2Cl2 (200 ml) and poured into cold 5% aqueous HCl (100 ml). The layers were separated and the organic phase washed with cold 5% aqueous HCl (50 ml) followed by brine (2×50 ml). The CH2Cl2 layer was dried (Na2SO4), filtered and evaporated in vacuo at 25° C. The resulting light yellow oil was pumped under reduced pressure for 2 hrs to provide 2-methanesulfonyloxydecane (6.5 g, 93.5%) as a light yellow oil. The reaction flask was immersed in an ice/water bath After stirring for 3 hrs The layers were separated the organic phase washed with cold 5% aqueous HCl (50 ml) The CH2Cl2 layer was dried (Na2SO4) filtered evaporated in vacuo at 25° C The resulting light yellow oil was pumped under reduced pressure for 2 hrs

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 2-decanol (5.0 ml, 26.0 mmol) in dry CH2Cl2 (52 ml) under an N2 atmosphere was added diisopropylethylamine (5.6 ml, 32.1 mmol). The reaction flask was immersed in an ice/water bath. After stirring for 10 minutes, methanesulfonyl chloride (2.8 ml, 36.1 mmol) was added via syringe over a period of 10 minutes. After stirring for 3 hrs, the reaction was diluted with cold CH2Cl2 (200 ml) and poured into cold 5% aqueous HCl (100 ml). The layers were separated and the organic phase washed with cold 5% aqueous HCl (50 ml) followed by brine (2×50 ml). The CH2Cl2 layer was dried (Na2SO4), filtered and evaporated in vacuo at 25° C. The resulting light yellow oil was pumped under reduced pressure for 2 hrs to provide 2-methanesulfonyloxydecane (6.5 g, 93.5%) as a light yellow oil. The reaction flask was immersed in an ice/water bath After stirring for 3 hrs The layers were separated the organic phase washed with cold 5% aqueous HCl (50 ml) The CH2Cl2 layer was dried (Na2SO4) filtered evaporated in vacuo at 25° C The resulting light yellow oil was pumped under reduced pressure for 2 hrs