ethyl 8-iodooctanoate

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

Procedure: NaH (0.39g, 9.6 mmol) was washed with hexane and then suspended in dry THF (45 mL). 5-Ethoxypentane-1-thiol (8.7 mmol) in THF (8 mL) was added and stirred for 1 h at room temperature. Ethyl 8-iodooctanoate (2.4 g, 8.7 mmol) in THF (7 mL) was added and the mixture was refluxed for 6 h. After evaporation of the solvent, the residue was taken into ethyl acetate (150 mL). The organic phase was washed with water (2 ×50 mL), brine (50 mL), and dried (Na2SO4). The crude product was purified by column chromatography on silica gel with ethyl acetate:hexane (1:5) and subsequent Kugelrohr distillation to give the title compound, ethyl 9-thia-12-oxatetradecanoate; yield 52%; bp 118° C.-120° C./0.15 torr; NMR: 1.2 (3H, t, J=7 Hz), 1.25 (3H, t, J=7 Hz), 1.2-1.8 (10 H, m), 2.28 (2H, t, J=6.5 Hz), 2.55 (2H, t, J=7 Hz), 2.67 (2H, t, J=7 Hz), 3.44 (2H, t, J=7 Hz), 3.66 (2H, t, J=7 Hz), and 4.1 ppm (2H, q, J=7 Hz). the mixture was refluxed for 6 h After evaporation of the solvent The organic phase was washed with water (2 ×50 mL), brine (50 mL) dried (Na2SO4) The crude product was purified by column chromatography on silica gel with ethyl acetate:hexane (1:5) and subsequent Kugelrohr distillation

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

Procedure: NaH (0.39g, 9.6 mmol) was washed with hexane and then suspended in dry THF (45 mL). 5-Ethoxypentane-1thiol (8.7 mmol) in THF (8 mL) was added and stirred for 1 h at room temperature. Ethyl 8-iodooctanoate (2.4 g, 8.7 mmol) in THF (7 mL) was added and the mixture was refluxed for 6 h. After evaporation of the solvent, the residue was taken into ethyl acetate (150 mL). The organic phase was washed with water (2×50 mL), brine (50 mL), and dried (Na2SO4). The crude product was purified by column chromatography on silica gel with ethyl acetate:hexane (1:5) and subsequent Kugelrohr distillation to give the title compound, ethyl 9-thia-12-oxatetradecanoate; yield 52%; bp 118°-120° C./0.15 torr; NMR: 1.2 (3H, t, J=7 Hz), 1.25 (3H, t, J=7 Hz), 1.2-1.8 (10 H, m), 2.28 (2H, t, J=6.5 Hz), 2.55 (2H, t, J=7 Hz), 2.67 (2H, t, J=7 Hz), 3.44 (2H, t, J=7 Hz), 3.66 (2H, t, J=7 Hz), and 4.1 ppm (2H, q, J=7 Hz). the mixture was refluxed for 6 h After evaporation of the solvent The organic phase was washed with water (2×50 mL), brine (50 mL) dried (Na2SO4) The crude product was purified by column chromatography on silica gel with ethyl acetate:hexane (1:5) and subsequent Kugelrohr distillation

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

Procedure: NaH (0.39g, 9.6 mmol) was washed with hexane and then suspended in dry THF (45 mL). 5-Ethoxypentane-1-thiol (8.7 mmol) in THF (8 mL) was added and stirred for 1 h at room temperature. Ethyl 8-iodooctanoate (2.4 g, 8.7 mmol) in THF (7 mL) was added and the mixture was refluxed for 6 h. After evaporation of the solvent, the residue was taken into ethyl acetate (150 mL). The organic phase was washed with water (2 ×50 mL), brine (50 mL), and dried (Na2SO4). The crude product was purified by column chromatography on silica gel with ethyl acetate:hexane (1:5) and subsequent Kugelrohr distillation to give the title compound, ethyl 9-thia-12-oxatetradecanoate; yield 52%; bp 118° C.-120° C./0.15 torr; NMR: 1.2 (3H, t, J=7 Hz), 1.25 (3H, t, J=7 Hz), 1.2-1.8 (10 H, m), 2.28 (2H, t, J=6.5 Hz), 2.55 (2H, t, J=7 Hz), 2.67 (2H, t, J=7 Hz), 3.44 (2H, t, J=7 Hz), 3.66 (2H, t, J=7 Hz), and 4.1 ppm (2H, q, J=7 Hz). the mixture was refluxed for 6 h After evaporation of the solvent The organic phase was washed with water (2 ×50 mL), brine (50 mL) dried (Na2SO4) The crude product was purified by column chromatography on silica gel with ethyl acetate:hexane (1:5) and subsequent Kugelrohr distillation