dodecanal

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

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

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: Then, the same reactor as above was charged with 226 g of acetyl-1,2-isopropylideneglycerol, 221 g of n-dodecanal and a solvent amount of toluene. Thereafter, p-toluenesulfonic acid was added as a catalyst and the acetal exchange reaction was carried out under reflux conditions. Then, a solution of sodium hydroxide in ethanol was added to decompose the ester moiety at the reflux temperature and the ethanol was distilled off under reduced pressure. The resulting crude product was extracted into diethyl ether and washed with 3 portions of distilled water. The diethyl ether layer was dehydrated over potassium carbonate and the diethyl ether was distilled off under reduced pressure. The residue was further purified by distillation under reduced pressure to provide 2-undecyl-4-hydroxymethyl-1,3-dioxolane. the ethanol was distilled off under reduced pressure The resulting crude product was extracted into diethyl ether washed with 3 portions of distilled water the diethyl ether was distilled off under reduced pressure The residue was further purified by distillation under reduced pressure

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

Procedure: n-Butyl lithium (a 2.5M solution in tetrahydrofuran; 0.42 ml, 1.04 mmol) was added dropwise to a solution of 4-(4,4-dibromo-3-butenyl)-2-triethylsilylfuran (200 mg, 0.51 mmol) in tetrahydrofuran (8 ml) at -78° under argon. After 2 hours, a solution of 1-dodecanal (102 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane to give the titled alcohol. was continued for 14 hours, while the cooling bath attained room temperature The mixture was quenched with water was extracted with ethyl ether Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane

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

Procedure: n-Butyl lithium (a 2.5M solution in tetrahydrofuran; 0.42 ml, 1.04 mmol) was added dropwise to a solution of 4-(4,4-dibromo-3-butenyl)-2-triethylsilylfuran (200 mg, 0.51 mmol) in tetrahydrofuran (8 ml) at -78 degrees under argon. After 2 hours, a solution of 1-dodecanal (102 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane to give the titled alcohol. was continued for 14 hours, while the cooling bath attained room temperature The mixture was quenched with water was extracted with ethyl ether Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane

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

Procedure: n-Butyl lithium (a 2.5M solution in tetrahydrofuran; 0.42 ml, 1.04 mmol) was added dropwise to a solution of 4-(4,4-dibromo-3-butenyl)-2-triethylsilylfuran (200 mg, 0.51 mmol) in tetrahydrofuran (8 ml) at -78 degrees under argon. After 2 hours, a solution of 1-dodecanal (102 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane to give the titled alcohol. was continued for 14 hours, while the cooling bath attained room temperature The mixture was quenched with water was extracted with ethyl ether Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane

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

Procedure: n-Butyl lithium (a 2.5M solution in tetrahydrofuran; 0.42 ml, 1.04 mmol) was added dropwise to a solution of 4-(4,4-dibromo-3-butenyl)-2-triethylsilylfuran (200 mg, 0.51 mmol) in tetrahydrofuran (8 ml) at -78 degrees under argon. After 2 hours, a solution of 1-dodecanal (102 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane to give the titled alcohol. was continued for 14 hours, while the cooling bath attained room temperature The mixture was quenched with water was extracted with ethyl ether Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane

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

Procedure: A mixture of potassium carbonate (1 equivalent) and morpholine (3.3 equivalents) were cooled to -5° under an inert atmosphere and dodecanal (1 equivalent) was added dropwise over 30 minutes. The reaction mixture was allowed to warm to room temperature and stirring was continued for 3-6 hours. Addition to ether followed by filtration and concentration gave crude morpholine enamine. The residue was distilled to give the desired product; b.p. 103-108° /0.07 mm; yield 74%. was added dropwise over 30 minutes followed by filtration and concentration gave crude morpholine enamine The residue was distilled

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

Procedure: A mixture of potassium carbonate (1 equivalent) and morpholine (3.3 equivalents) were cooled to -5° under an inert atmosphere and dodecanal (1 equivalent) was added dropwise over 30 minutes. The reaction mixture was allowed to warm to room temperature and stirring was continued for 3-6 hours. Addition to ether followed by filtration and concentration gave crude morpholine enamine. The residue was distilled to give the desired product; b.p. 103-108° /0.07 mm; yield 74%. was added dropwise over 30 minutes followed by filtration and concentration gave crude morpholine enamine The residue was distilled

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

Procedure: n-Butyl lithium (a 2.5M solution in tetrahydrofuran; 0.42 ml, 1.04 mmol) was added dropwise to a solution of 4-(4,4-dibromo-3-butenyl)-2-triethylsilylfuran (200 mg, 0.51 mmol) in tetrahydrofuran (8 ml) at -78 degrees under argon. After 2 hours, a solution of 1-dodecanal (102 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane to give the titled alcohol. was continued for 14 hours, while the cooling bath attained room temperature The mixture was quenched with water was extracted with ethyl ether Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane