dodecyl 2-bromopropanoate

Conditions: temp:57.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 1-decanol 2 (10 g, 53.7 mmol) in toluene (100 mL) was added triethylamine (7.5 mL, 53.7 mmol)) followed by 2-bromo propionyl bromide 58 (12.7 g, 59.1 mmol) at 5-10° C. The reaction mixture was stirred for 3 hours at 55-60° C.; the reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirred for 15 minutes at 25-35° C. The aqueous and organic layers were separated, the organic layer was washed with brine, and the combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 59 (16.2 g, yield: 94%) as a liquid. The reaction mixture was quenched with saturated sodium bicarbonate solution stirred for 15 minutes at 25-35° C The aqueous and organic layers were separated the organic layer was washed with brine the combined organic layers were washed with brine solution The organic layer was dried over Na2SO4 concentrated under vacuum

Conditions: temp:57.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 1-decanol 2 (10 g, 53.7 mmol) in toluene (100 mL) was added triethylamine (7.5 mL, 53.7 mmol)) and followed by 2-bromo propionyl bromide 58 (12.7 g, 59.1 mmol) at 5-10° C. The reaction mixture was stirred for 3 hour at 55-60° C., and the reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirred for 15 minutes at 25-35° C. The aqueous and organic layers were separated, the organic layer was washed with brine, and the combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 59 (16.2 g, yield: 94%) as a liquid. The reaction mixture was quenched with saturated sodium bicarbonate solution stirred for 15 minutes at 25-35° C The aqueous and organic layers were separated the organic layer was washed with brine the combined organic layers were washed with brine solution The organic layer was dried over Na2SO4 concentrated under vacuum

Conditions: temp:57.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 59 (10 g, 31.2 mmol) in acetonitrile (30 mL) was added sodium bicarbonate (2.62 g, 31.2 mmol) and followed by isopropyl amine (50% in water) (30 mL, 3 vol) at 25-30° C. The reaction mixture was stirred for 12 h at 55-60° C. and the reaction was monitored by TLC. The solid obtained in the reaction mixture was filtered under vacuum. The solvent was concentrated, diluted with ethyl acetate/water and stirred for 15 minutes at 25-30° C. The aqueous and organic layers were separated, and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 62 (7 g, yield: 75.2%) as a liquid. The solid obtained in the reaction mixture was filtered under vacuum The solvent was concentrated diluted with ethyl acetate/water stirred for 15 minutes at 25-30° C The aqueous and organic layers were separated the aqueous layer was extracted with ethyl acetate (2×10 mL) The combined organic layers were washed with brine solution The organic layer was dried over Na2SO4 concentrated under vacuum

Conditions: temp:57.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 1-decanol 2 (10 g, 53.7 mmol) in toluene (100 mL) was added triethylamine (7.5 mL, 53.7 mmol)), followed by 2-bromo propionyl bromide 58 (12.7 g, 59.1 mmol) at 5-10° C. The reaction mixture was stirred for 3 hour at 55-60° C. and the reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirred for 15 minutes at 25-35° C. The aqueous and organic layers were separated, the organic layer was washed with brine, and the combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 59 (16.2 g, yield: 94%) as a liquid. The reaction mixture was quenched with saturated sodium bicarbonate solution stirred for 15 minutes at 25-35° C The aqueous and organic layers were separated the organic layer was washed with brine the combined organic layers were washed with brine solution The organic layer was dried over Na2SO4 concentrated under vacuum

Conditions: temp:27.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 59 (10 g, 31.2 mmol) in acetonitrile (20 mL) was added sodium bicarbonate (2.62 g, 31.2 mmol) and followed by mono methyl amine (40% in water) (30 mL, 3 vol) at 25-30° C. The reaction mixture was stirred for 3 hour at 25-30° C.; the reaction was monitored by TLC. The solid obtained in the reaction mixture was filtered under vacuum. The solvent was concentrated, diluted with ethyl acetate/water and stirred for 15 minutes at 25-30° C. The aqueous and organic layers were separated, and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine solution, dried over Na2SO4 and concentrated under vacuum to afford crude 60 (7 g, yield: 82.3%) as a liquid The solid obtained in the reaction mixture was filtered under vacuum The solvent was concentrated diluted with ethyl acetate/water stirred for 15 minutes at 25-30° C The aqueous and organic layers were separated the aqueous layer was extracted with ethyl acetate (2×10 mL) The combined organic layers were washed with brine solution dried over Na2SO4 concentrated under vacuum

Conditions: temp:57.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 1-decanol 2 (10 g, 53.7 mmol) in toluene (100 mL) was added triethylamine (7.5 mL, 53.7 mmol)) and followed by 2-bromo propionyl bromide 58 (12.7 g, 59.1 mmol) at 5-10° C. The reaction mixture was stirred for 3 hour at 55-60° C., and the reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirred for 15 minutes at 25-35° C. The aqueous and organic layers were separated, the combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 59 (16.19 g, yield: 94%) as a liquid. The reaction mixture was quenched with saturated sodium bicarbonate solution stirred for 15 minutes at 25-35° C The aqueous and organic layers were separated the combined organic layers were washed with brine solution The organic layer was dried over Na2SO4 concentrated under vacuum