1-bromopentadecane

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

Procedure: 2-(heptadecyl)furan (4) was prepared exactly as described above for 2-(pentadecyl)furan, substituting 1-bromo heptadecane for 1-bromopentadecane. The chromatographed product was recrystallized from methanol as described above to afford of 2-(heptadecyl)furan (4) in 48% yield. 2-(heptadecyl)furan (4) was prepared exactly The chromatographed product was recrystallized from methanol

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A dry 50 ml round bottom flask charged with furan (1.40 g, 20.6 mmol) and THF (10 ml), was cooled to -78° C. and n-butyllithium (13.6 ml, 1.50 M in hexanes, 20.6 mmol) was added dropwise. The solution was stirred for 30 mm at -78° C., then warmed to 0° C. and placed in an ice bath for 1 h. The mixture was then cooled to -78° C. and 1-bromopentadecane 9 (5 g, 17.2 mmol) in THF (10 ml) were added dropwise. The resulting solution was stirred for 1 h, then warmed to room temp and stirred 12 h. The reaction was quenched with a saturated solution of NH4Cl (5 ml). The organic layer was separated and the aqueous layer extracted with ether (3×20 ml). The combined organic layers were washed with saturated NaHCO3 (1×20 ml), brine (1×20 ml), dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by flash chromatography on silica, eluting with hexanes to afford a oily liquid that was recrystallized from methanol (~ 50 ml/g, cooling to 5° C.) to afford 4.8 g (64%) of 2-(pentadecyl)furan (1). warmed to 0° C. The mixture was then cooled to -78° C. The resulting solution was stirred for 1 h warmed to room temp stirred 12 h The reaction was quenched with a saturated solution of NH4Cl (5 ml) The organic layer was separated the aqueous layer extracted with ether (3×20 ml) The combined organic layers were washed with saturated NaHCO3 (1×20 ml), brine (1×20 ml) dried over MgSO4 filtered concentrated under vacuum The crude product was purified by flash chromatography on silica eluting with hexanes to afford a oily liquid that was recrystallized from methanol (~ 50 ml/g, cooling to 5° C.)

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

Procedure: 1-Bromopentadecane is reacted in the usual way with ethyl β-mercaptopropionate and the syrup obtained reduced with lithium aluminium hydride to give a yield of 84% of theory of 3-pentadecylthiopropanol; m.p. 36°-39° C. the syrup obtained

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

Procedure: This was prepared using a similar method to that described for compound 3. Quantities: compound 1 (2.31 g, 12.1 mmol), 1-bromopentadecane (3.97 g, 13.6 mmol), potassium carbonate (2.97 g, 21.5 mmol) and butanone (80 ml). This was prepared

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1-bromopentadecane (0.0051 mole) in DMF (18 ml) was added dropwise at room temperature to a mixture of intermediate (10) (0.00483 mole) and NaHCO3 (0.0051 mole) in DMF (10 ml). The mixture was stirred at 70° C. for 5 hours and at 45° C. overnight, then brought to room temperature. H2O and NaCl were added. The mixture was extracted with EtOAc. The organic layer was separated, washed with a saturated NaCl solution, dried (MgSO4), filtered and the solvent was evaporated. The residue (3.8 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15-40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.49 g of compound 2 having a melting point of 80° C. and represented by the formula brought to room temperature The mixture was extracted with EtOAc The organic layer was separated washed with a saturated NaCl solution dried (MgSO4) filtered the solvent was evaporated The residue (3.8 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15-40 μm) The pure fractions were collected the solvent was evaporated

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

Procedure: According to the method of Example 26, from aldehyde 8 (680 mg, 3.1 mmol) and 1-bromopentadecane (6.55 g, 22.5 mmol), alcohol 92 was obtained as a colorless oil (800 mg, 60% yield).

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

Procedure: According to the method of Example 26, from aldehyde 28 (640 mg, 3.1 mmol) and 1-bromopentadecane (5.0 g, 17.2 mmol), alcohol 90 was obtained as a colorless oil (690 mg, 53% yield).

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

Procedure: According to the method of Example 26, from aldehyde 26 (445 mg, 1.76 mmol) and 1-bromopentadecane (1.28 g, 4.39 mmol), alcohol 80 was obtained as a colorless oil (422 mg, 52% yield).

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

Procedure: According to the method of Example 26, from aldehyde 23 (503 mg, 1.05 mmol) and 1-bromopentadecane (768; mg, 2.64 mmol), alcohol 77 was obtained as a colorless oil (350 mg, 48% yield).

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

Procedure: According to the method of Example 26, from aldehyde 20 (597 mg, 1.37 mmol) and 1-bromopentadecane (999 mg, 3.43 mmol), alcohol 74 was obtained as a colorless oil (496 mg, 56% yield).

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

Procedure: According to the method of Example 26, from aldehyde 20 (597 mg, 1.37 mmol) and 1-bromopentadecane (999 mg, 3.43 mmol), alcohol 74 was obtained as a colorless oil (496 mg, 56% yield).

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

Procedure: According to the method of Example 26, from aldehyde 17 (470 mg, 1.59 mmol) and 1-bromopentadecane (0.63 mL, 3.18 mmol), alcohol 71 was obtained as a colorless oil (499 mg, 60% yield).