tetradecanal

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

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

Procedure: IR (thin film) 2920, 2850, 1725, 1465, 1265, 1175, 1045 cm-1 ;1H NMR (CDCl3, 300 MHz) δ 7.00 (dt, 1, J=15.5, 6.8 Hz, CH2CH=), 5.84 (dt, 1 J=15.5, 1.2 Hz, COCH=), 4.21 (dd, 2, J=14.2, 7.2 Hz, CH2O), 2.23 (qd, 2, J=6.9, 1.2 Hz, CH2CH=), 1.49 (t, 2, J=7 Hz, CH2CH2CH3), 1.3 (m, 20, CH2CH2CH2), 0.92 (t, 3, J=7 Hz, CH2CH2CH3). Rf (5% ethyl acetate:hexanes): tetradecanal, 0.29; ester product, 0 31. MS (FD): m/e 282 (M+).

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

Procedure: IR (thin film) 2920, 2850, 1725, 1465, 1265, 1175, 1045 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ7.00 (dt, 1, J=15.5, 6.8 Hz, CH2CH=), 5.84 (dt, 1, J=15.5, 1.2 Hz, COCH=), 4.21 (dd, 2, J=14.2, 7.2 Hz, CH2O), 2.23 (qd, 2, J=6.9, 1.2 Hz, CH2CH=), 1.49 (t, 2, J=7 Hz, CH2CH2CH3), 1.3 (m, 20, CH2CH2CH2), 0.92 (t, 3, J=7 Hz, CH2CH2CH3). Rf (5% ethyl acetate:hexanes):tetradecanal, 0.29; ester product, 0.31. MS (FD): m/e 282 (M+).

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of oxalylchloride (8.0 mL, 88.0 mmol, 2.2 eq.) in abs. dichloromethane (200 mL) was treated with DMSO (13.6 mL, 192 mmol, 4.8 eq.) at −60° C. After 3 min the reaction mixture was warmed to approx. 15° C. Then a solution of tetradecan-1-ol (8.56 g, 40.0 mmol) in dry dichloromethane (40 mL) and after further 3 min triethylamine (28 mL, 200 mmol, 5.0 eq.) were added. Then the reaction mixture was slowly warmed to 5° C. and quenched by addition of water (200 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (3×100 mL). The combined organic phases were washed with brine (1×200 mL) and dried over MgSO4. The solvent was removed under reduced pressure and the product was isolated as a white solid, which was used in the next reaction without purification. Yield: 10.4 g (100%), purity: 98% (GC). Then the reaction mixture was slowly warmed to 5° C. quenched by addition of water (200 mL) The phases were separated the aqueous phase was extracted with dichloromethane (3×100 mL) The combined organic phases were washed with brine (1×200 mL) dried over MgSO4 The solvent was removed under reduced pressure the product was isolated as a white solid, which was used in the next reaction without purification

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

Procedure: The compound was prepared as described in example 2/4, reacting the indole with tetradecane aldehyde. Yield 80%. The compound was prepared

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

Procedure: The compound was prepared as described in example 2/4, reacting the indole with tetradecane aldehyde. Yield 80%. The compound was prepared

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

Procedure: To an ice-cooled solution of tetradecanal (18.75 g) in diethyl ether (100 ml) was added acetic acid (5.66 ml) and potassium cyanide (6.64 g). The mixture was warmed to room temperature and stirred for 72 hours. The resulting solution was washed with water, and the aqueous phase was extracted with diethyl ether (50 ml). The combined organic phase was dried, and concentrated to dryness. The residue was purified by silica gel chromatography and triturated in diisopropyl ether (10 ml) to give 2-hydroxypentadecanenitrile (4.66 g). The resulting solution was washed with water the aqueous phase was extracted with diethyl ether (50 ml) The combined organic phase was dried concentrated to dryness The residue was purified by silica gel chromatography triturated in diisopropyl ether (10 ml)

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

Procedure: 32.3 g (150 mmol) of pyridinium chlorochromate are suspended in 200 ml of anhydrous methylene chloride at room temperature, with vigorous stirring, and a solution of 21.4 g (100 mmol) of tetradecanol in 20 ml of anhydrous methylene chloride is added. This results in the reaction mixture boiling. The reaction is complete after 11/2 hours. The solution is decanted off from the solid which is washed with about 200 ml of dry diethyl ether. After filtration and evaporation of the solvent, chromatography is carried out on silica gel using petroleum ether (boiling point 35°-80° C.)/ethyl acetate 9:1. Yield: 18 g (84%). This results in the reaction mixture 2 hours The solution is decanted off from the solid which is washed with about 200 ml of dry diethyl ether After filtration and evaporation of the solvent, chromatography

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

Procedure: IR (thin film) 2920, 2850, 1725, 1465, 1265, 1175, 1045 cm-1 ;1H NMR (CDCl3, 300 MHz) δ 7.00 (dt, 1, J=15.5, 6.8 Hz, CH2CH=), 5.84 (dt, 1 J=15.5, 1.2 Hz, COCH=), 4.21 (dd, 2, J=14.2, 7.2 Hz, CH2O), 2.23 (qd, 2, J=6.9, 1.2 Hz, CH2CH=), 1.49 (t, 2, J=7 Hz, CH2CH2CH3), 1.3 (m, 20, CH2CH2CH2), 0.92 (t, 3, J=7 Hz, CH2CH2CH3). Rf (5% ethyl acetate:hexanes): tetradecanal, 0.29; ester product, 0 31. MS (FD): m/e 282 (M+).

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

Procedure: IR (thin film) 2920, 2850, 1725, 1465, 1265, 1175, 1045 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ7.00 (dt, 1, J=15.5, 6.8 Hz, CH2CH=), 5.84 (dt, 1, J=15.5, 1.2 Hz, COCH=), 4.21 (dd, 2, J=14.2, 7.2 Hz, CH2O), 2.23 (qd, 2, J=6.9, 1.2 Hz, CH2CH=), 1.49 (t, 2, J=7 Hz, CH2CH2CH3), 1.3 (m, 20, CH2CH2CH2), 0.92 (t, 3, J=7 Hz, CH2CH2CH3). Rf (5% ethyl acetate:hexanes):tetradecanal, 0.29; ester product, 0.31. MS (FD): m/e 282 (M+).

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of oxalylchloride (8.0 mL, 88.0 mmol, 2.2 eq.) in abs. dichloromethane (200 mL) was treated with DMSO (13.6 mL, 192 mmol, 4.8 eq.) at −60° C. After 3 min the reaction mixture was warmed to approx. 15° C. Then a solution of tetradecan-1-ol (8.56 g, 40.0 mmol) in dry dichloromethane (40 mL) and after further 3 min triethylamine (28 mL, 200 mmol, 5.0 eq.) were added. Then the reaction mixture was slowly warmed to 5° C. and quenched by addition of water (200 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (3×100 mL). The combined organic phases were washed with brine (1×200 mL) and dried over MgSO4. The solvent was removed under reduced pressure and the product was isolated as a white solid, which was used in the next reaction without purification. Yield: 10.4 g (100%), purity: 98% (GC). Then the reaction mixture was slowly warmed to 5° C. quenched by addition of water (200 mL) The phases were separated the aqueous phase was extracted with dichloromethane (3×100 mL) The combined organic phases were washed with brine (1×200 mL) dried over MgSO4 The solvent was removed under reduced pressure the product was isolated as a white solid, which was used in the next reaction without purification

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

Procedure: The compound was prepared as described in example 2/4, reacting the indole with tetradecane aldehyde. Yield 80%. The compound was prepared