2-dodecylfuran

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-dodecylfuran (1.00 g, 4.24 mmol) and NaHCO3 (712 mg, 8.48 mmol) in acetone/H2O (10:1, 2 ml) was treated at −20° C. with NBS (905 mg, 5.11 mmol) dissolved in acetone/H2O (10 ml). After the mixture had been stirred for 1 h at −20° C., it was treated with pyridine (0.69 ml, 8.48 mmol). Thereafter, the reaction mixture came to RT, and stirring was continued for 2 h. The solution was washed with 1 N HCl, followed by extraction with ethyl acetate (2×50 ml). The organic phase was dried over NaSO4 and concentrated in order to obtain the crude product. The latter was purified by column chromatography (DCM) to give the product as a pale yellow oil (642 mg, 2.55 mmol, 60%). 1H NMR (300 MHz, CDCl3) δ 1H ppm: 0.88 (t, 3H, J=6.7 Hz, H-16), 1.19-1.36 (m, 18H), 1.59-1.71 (m, H-5), 2.69 (t, 2H, J=7.8 Hz, H-5), 6.73-6.92 (m, 2H, H-2.3), 9.78 (d, CHO, J=7.0 Hz, H-1); 13C NMR (75.5 MHz, CDCl3) δ 13C ppm: 14.2 (C-16), 22.8, 23.7, 29.2, 29.3, 29.4, 29.5, 29.5, 29.6, 29.7, 32.0, 41.3 (C-5), 137.2 (C-2), 144.8 (C-3), 193.2 (C-1), 199.9 (C-4); (−)-ESI-CID-MS: 251 [M−H]−; ESI-FT-ICR-MS: m/z 251.20137 (calculated for C16H27O2−, m/z 251.20165). came to RT stirring was continued for 2 h The solution was washed with 1 N HCl followed by extraction with ethyl acetate (2×50 ml) The organic phase was dried over NaSO4 concentrated in order to obtain the crude product The latter was purified by column chromatography (DCM)

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-dodecylfuran (1.00 g, 4.24 mmol) and NaHCO3 (712 mg, 8.48 mmol) in acetone/H2O (10:1, 2 ml) was treated at −20° C. with NBS (905 mg, 5.11 mmol) dissolved in acetone/H2O (10 ml). After the mixture had been stirred for 1 h at −20° C., it was treated with pyridine (0.69 ml, 8.48 mmol). Thereafter, the reaction mixture came to RT, and stirring was continued for 2 h. The solution was washed with 1 N HCl, followed by extraction with ethyl acetate (2×50 ml). The organic phase was dried over NaSO4 and concentrated in order to obtain the crude product. The latter was purified by column chromatography (DCM) to give the product as a pale yellow oil (642 mg, 2.55 mmol, 60%). 1H NMR (300 MHz, CDCl3) δ 1H ppm: 0.88 (t, 3H, J=6.7 Hz, H-16), 1.19-1.36 (m, 18H), 1.59-1.71 (m, H-5), 2.69 (t, 2H, J=7.8 Hz, H-5), 6.73-6.92 (m, 2H, H-2.3), 9.78 (d, CHO, J=7.0 Hz, H-1); 13C NMR (75.5 MHz, CDCl3) δ 13C ppm: 14.2 (C-16), 22.8, 23.7, 29.2, 29.3, 29.4, 29.5, 29.5, 29.6, 29.7, 32.0, 41.3 (C-5), 137.2 (C-2), 144.8 (C-3), 193.2 (C-1), 199.9 (C-4); (−)-ESI-CID-MS: 251 [M−H]−; ESI-FT-ICR-MS: m/z 251.20137 (calculated for C16H27O2−, m/z 251.20165). came to RT stirring was continued for 2 h The solution was washed with 1 N HCl followed by extraction with ethyl acetate (2×50 ml) The organic phase was dried over NaSO4 concentrated in order to obtain the crude product The latter was purified by column chromatography (DCM)

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-dodecylfuran (1.00 g, 4.24 mmol) and NaHCO3 (712 mg, 8.48 mmol) in acetone/H2O (10:1, 2 ml) was treated at −20° C. with NBS (905 mg, 5.11 mmol) dissolved in acetone/H2O (10 ml). After the mixture had been stirred for 1 h at −20° C., it was treated with pyridine (0.69 ml, 8.48 mmol). Thereafter, the reaction mixture came to RT, and stirring was continued for 2 h. The solution was washed with 1 N HCl, followed by extraction with ethyl acetate (2×50 ml). The organic phase was dried over NaSO4 and concentrated in order to obtain the crude product. The latter was purified by column chromatography (DCM) to give the product as a pale yellow oil (642 mg, 2.55 mmol, 60%). 1H NMR (300 MHz, CDCl3) δ 1H ppm: 0.88 (t, 3H, J=6.7 Hz, H-16), 1.19-1.36 (m, 18H), 1.59-1.71 (m, H-5), 2.69 (t, 2H, J=7.8 Hz, H-5), 6.73-6.92 (m, 2H, H-2.3), 9.78 (d, CHO, J=7.0 Hz, H-1); 13C NMR (75.5 MHz, CDCl3) δ 13C ppm: 14.2 (C-16), 22.8, 23.7, 29.2, 29.3, 29.4, 29.5, 29.5, 29.6, 29.7, 32.0, 41.3 (C-5), 137.2 (C-2), 144.8 (C-3), 193.2 (C-1), 199.9 (C-4); (−)-ESI-CID-MS: 251 [M−H]−; ESI-FT-ICR-MS: m/z 251.20137 (calculated for C16H27O2−, m/z 251.20165). came to RT stirring was continued for 2 h The solution was washed with 1 N HCl followed by extraction with ethyl acetate (2×50 ml) The organic phase was dried over NaSO4 concentrated in order to obtain the crude product The latter was purified by column chromatography (DCM)

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

Procedure: A solution of 30.4 g (0.2 moles) of 2-dodecylfuran in 300 ml of anhydrous ether is stirred at -20° C. after which 0.22 moles (92 ml of a 2.4 molar hexane solution) of butyllithium is added slowly with stirring. The reaction mixture is stirred for 1 hour then poured over 200 g of crushed dry ice (solid CO2) after which the mixture is allowed to stand for 1 hour prior to dilution with a saturated ammonium chloride solution The organic layer is separated, washed with water and brine, dried over sodium sulfate and evaporated to give 5-dodecyl-2-furancarboxylic acid. The thus obtained acid in 500 ml of anhydrous ether is stirred at room temperature during which time 200 ml of a 2 molar solution of methyllithium in ether is added slowly. The reaction mixture is allowed to stand at room temperature for 2 hours after which it is poured into a saturated ammonium chloride solution The organic layer is separated and washed with water and brine, dried over sodium sulfate and evaporated to dryness to give white crystals of methyl 2-(5-dodecylfuryl) ketone. M.P. 35°-7° C. is added slowly The reaction mixture is stirred for 1 hour to dilution with a saturated ammonium chloride solution The organic layer is separated washed with water and brine dried over sodium sulfate evaporated

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

Procedure: A mixture of 68.1 g (1.0 mole) of furan and 500 ml of anhydrous ether is stirred at -20° C. after which 1.1 moles (458 ml of a 2.4 molar hexane solution) of butyllithium is added slowly with stirring. The reaction mixture is stirred for 1 hour, then 284 g (1.2 moles) of 1-bromododecane is added. The reaction mixture is stirred at room temperature for 4 hours after which it is poured into a saturated ammonium chloride solution. The organic layer is separated and washed with water and brine, dried over sodium sulfate and distilled under reduced pressure to give 2-dodecylfuran. is added slowly The reaction mixture is stirred for 1 hour The reaction mixture is stirred at room temperature for 4 hours after which it The organic layer is separated washed with water and brine dried over sodium sulfate distilled under reduced pressure

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-dodecylfuran (1.00 g, 4.24 mmol) and NaHCO3 (712 mg, 8.48 mmol) in acetone/H2O (10:1, 2 ml) was treated at −20° C. with NBS (905 mg, 5.11 mmol) dissolved in acetone/H2O (10 ml). After the mixture had been stirred for 1 h at −20° C., it was treated with pyridine (0.69 ml, 8.48 mmol). Thereafter, the reaction mixture came to RT, and stirring was continued for 2 h. The solution was washed with 1 N HCl, followed by extraction with ethyl acetate (2×50 ml). The organic phase was dried over NaSO4 and concentrated in order to obtain the crude product. The latter was purified by column chromatography (DCM) to give the product as a pale yellow oil (642 mg, 2.55 mmol, 60%). 1H NMR (300 MHz, CDCl3) δ 1H ppm: 0.88 (t, 3H, J=6.7 Hz, H-16), 1.19-1.36 (m, 18H), 1.59-1.71 (m, H-5), 2.69 (t, 2H, J=7.8 Hz, H-5), 6.73-6.92 (m, 2H, H-2.3), 9.78 (d, CHO, J=7.0 Hz, H-1); 13C NMR (75.5 MHz, CDCl3) δ 13C ppm: 14.2 (C-16), 22.8, 23.7, 29.2, 29.3, 29.4, 29.5, 29.5, 29.6, 29.7, 32.0, 41.3 (C-5), 137.2 (C-2), 144.8 (C-3), 193.2 (C-1), 199.9 (C-4); (−)-ESI-CID-MS: 251 [M−H]−; ESI-FT-ICR-MS: m/z 251.20137 (calculated for C16H27O2−, m/z 251.20165). came to RT stirring was continued for 2 h The solution was washed with 1 N HCl followed by extraction with ethyl acetate (2×50 ml) The organic phase was dried over NaSO4 concentrated in order to obtain the crude product The latter was purified by column chromatography (DCM)