2-methylundecanal

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

Procedure: Starting from (4-methoxyphenyl)methyltriphenylphosphonium bromide (6.00 g, 13.0 mmol, 1.0 equiv.), KtBuO (14 mL, 14.2 mmol, 1.1 equiv., 1M in THF) and 2-methylundecanal (2.86 g, 15.5 mmol, 1.2 equiv.), 1.98 g (53%) of the title compound was obtained after purification by flash chromatography on SiO2 (hexane/EtOAc 99:1) as a colorless oil.

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Starting from (1-(2-naphthyl)ethyltriphenylphosphonium bromide (6.40 g, 12.9 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 8.0 mL, 12.9 mmol, 1.0 equiv.) and 2-methylundecanal (3.56 g, 19.3 mmol, 1.5 equiv.), and after stirring the mixture at 25° C. for 3 h, 0.94 g (23%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of benzyltriphenylphosphonium bromide (3.20 g, 7.38 mmol, 1.0 equiv.) in THF (14 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 4.6 mL, 7.38 mmol, 1.0 equiv.) at 0° C., the red suspension was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 2-methylundecanal (2.04 g, 11.1 mmol, 1.5 equiv.) in THF (5 mL) was added, and the mixture was stirred at 65° C. for 18 h. After addition of H2O, the aqueous layer was extracted with cyclohexane (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane) to yield 1.45 g (76%) of the title compound as a colorless oil. The mixture was re-cooled to 0° C. the mixture was stirred at 65° C. for 18 h the aqueous layer was extracted with cyclohexane (2×) the combined organic phases were washed with brine dried (MgSO4) filtered the filtrate was concentrated The residue was purified by flash chromatography on SiO2 (cyclohexane)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: p-Methylphenethyltriphenylphosphonium bromide (2.90 g, 6.29 mmol, 1.0 equiv.) in THF (12 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 3.9 mL, 6.29 mmol, 1.0 equiv.) at 0° C., the red solution was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 2-methylundecanal (1.74 g, 9.43 mmol, 1.5 equiv.) in THF (5 mL) was added, and the mixture was stirred at 65° C. for 16 h. After addition of H2O, the aqueous layer was extracted with cyclohexane (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3) to yield 1.24 g (69%) of the title compound as a colorless oil. The mixture was re-cooled to 0° C. the mixture was stirred at 65° C. for 16 h the aqueous layer was extracted with cyclohexane (2×) the combined organic phases were washed with brine dried (MgSO4) filtered the filtrate was concentrated The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3)

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: p-Methoxyphenethyltriphenylphosphonium bromide (3.40 g, 7.12 mmol, 1.0 equiv.) in THF (14 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 4.5 mL, 7.12 mmol, 1.0 equiv.) at 0° C., the red solution was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 2-methylundecanal (1.97 g, 10.7 mmol, 1.5 equiv.) in THF (6 mL) was added, and the mixture was stirred at 70° C. for 14 h. After addition of H2O, the aqueous layer was extracted with cyclohexane (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 98:2) to yield 1.36 g (63%) of the title compound as a light yellow oil. The mixture was re-cooled to 0° C. the mixture was stirred at 70° C. for 14 h the aqueous layer was extracted with cyclohexane (2×) the combined organic phases were washed with brine dried (MgSO4) filtered the filtrate was concentrated The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 98:2)

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

Procedure: Starting from phenethyltriphenylphosphonium bromide (3.60 g, 8.05 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 5.0 mL, 8.05 mmol, 1.0 equiv.) and 2-methylundecanal (2.25 g, 12.1 mmol, 1.5 equiv.), 1.33 g (61%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (hexanes).

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

Procedure: Starting from phenethyltriphenylphosphonium bromide (3.60 g, 8.05 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 5.0 mL, 8.05 mmol, 1.0 equiv.) and 2-methylundecanal (2.25 g, 12.1 mmol, 1.5 equiv.), 1.33 g (61%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (hexanes).

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Methylundecanal (4.61 g, 5.55 ml, 0.025 mol), tetraethylene glycol (97.1 g, 86.3 ml, 0.5 mol) and 10% Pd/C (0.3 g, 6.5 wt % to n-decanal) are charged to a 150 ml Parr reactor. The system is purged with nitrogen three times. Then 500 psi of hydrogen is charged, the reactor is heated to 200° C., and the hydrogen pressure is adjusted to 1000 psi. After 3 hours at 200° C. and 1000 psi, GC analysis shows 99.5% conversion of 2-methyl-undecanal and detect 11-methyl-3,6,9,12-tetraoxa-1-tricosanol (82.3%) and 2-methyundecanol (7.9%). The system is purged with nitrogen three times Then 500 psi of hydrogen is charged

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Methylundecanal (4.61 g, 5.55 ml, 0.025 mol), triethylene glycol (75.1 g, 66.8 ml, 0.5 mol) and 10% Pd/C (0.3 g, 6.5 wt % to n-decanal) are charged to a 150 ml Parr reactor. The system is purged with nitrogen three times. Then 500 psi of hydrogen are charged, the reactor is heated to 200° C., and the hydrogen pressure is adjusted to 1000 psi. After 3 hours at 200° C. and 1000 psi, GC analysis shows 99.7% conversion of 2-methyl-undecanal and detects 11-methyl-3,6,9-trioxa-1-eicosanol (76.3%) and 2-methyundecanol (11.9%). The system is purged with nitrogen three times Then 500 psi of hydrogen are charged

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

Procedure: Starting from (4-methoxyphenyl)methyltriphenylphosphonium bromide (6.00 g, 13.0 mmol, 1.0 equiv.), KtBuO (14 mL, 14.2 mmol, 1.1 equiv., 1M in THF) and 2-methylundecanal (2.86 g, 15.5 mmol, 1.2 equiv.), 1.98 g (53%) of the title compound was obtained after purification by flash chromatography on SiO2 (hexane/EtOAc 99:1) as a colorless oil.

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Starting from (1-(2-naphthyl)ethyltriphenylphosphonium bromide (6.40 g, 12.9 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 8.0 mL, 12.9 mmol, 1.0 equiv.) and 2-methylundecanal (3.56 g, 19.3 mmol, 1.5 equiv.), and after stirring the mixture at 25° C. for 3 h, 0.94 g (23%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of benzyltriphenylphosphonium bromide (3.20 g, 7.38 mmol, 1.0 equiv.) in THF (14 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 4.6 mL, 7.38 mmol, 1.0 equiv.) at 0° C., the red suspension was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 2-methylundecanal (2.04 g, 11.1 mmol, 1.5 equiv.) in THF (5 mL) was added, and the mixture was stirred at 65° C. for 18 h. After addition of H2O, the aqueous layer was extracted with cyclohexane (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane) to yield 1.45 g (76%) of the title compound as a colorless oil. The mixture was re-cooled to 0° C. the mixture was stirred at 65° C. for 18 h the aqueous layer was extracted with cyclohexane (2×) the combined organic phases were washed with brine dried (MgSO4) filtered the filtrate was concentrated The residue was purified by flash chromatography on SiO2 (cyclohexane)