undec-10-enoic acid

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: Glassware used for surface modification was cleaned with organic solvents and etched overnight in basic detergent solution. Prior to use, it was rinsed with ultrapure water and dried at 120° C. 1-Hexadecene (98%, Sigma-Aldrich) was purified by column chromatography and vacuum distillation. 1-Hexadecyne was obtained by reacting 1-bromotetradecane with lithium acetylide ethylenediamine complex in dimethylsulfoxide. 11-Fluoroundec-1-ene was synthesized as described elsewhere.14 2,2,2-Trifluoroethyl undec-10-ynoate and 2,2,2-trifluoroethyl undec-10-enoate were synthesized by esterification of 10-undecynoic acid, respectively 10-undecenoic acid, with 2,2,2-trifluoroethanol using N,N′-dicyclohexylcarbodiimide as a coupling reagent and 4-dimethylaminopyridine as a catalyst. Solvents used were either of analytical grade or distilled prior to use. distilled

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

Procedure: Glassware used for surface modification was cleaned with organic solvents and etched overnight in basic detergent solution. Prior to use, it was rinsed with ultrapure water and dried at 120° C. 1-Hexadecene (98%, Sigma-Aldrich) was purified by column chromatography and vacuum distillation. 1-Hexadecyne was obtained by reacting 1-bromotetradecane with lithium acetylide ethylenediamine complex in dimethylsulfoxide. 11-Fluoroundec-1-ene was synthesized as described elsewhere.14 2,2,2-Trifluoroethyl undec-10-ynoate and 2,2,2-trifluoroethyl undec-10-enoate were synthesized by esterification of 10-undecynoic acid, respectively 10-undecenoic acid, with 2,2,2-trifluoroethanol using N,N′-dicyclohexylcarbodiimide as a coupling reagent and 4-dimethylaminopyridine as a catalyst. Solvents used were either of analytical grade or distilled prior to use. distilled

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

Procedure: An oven-dried 50 mL round bottom flask was charged with 3-aminoquinuclidine dihydrochloride (2 mmol), 10-undecenoic acid (2 mmol), N,N-dimethylaminopyridine (0.3 mmol), diisopropylethylamine (4 mmol), and dry DMF (15 mL). The flask was purged with argon and cooled to 0° C. in an ice bath. Dicyclohexycarbodiimide (2.2 mmol) was then add to the solution, the flask repurged with argon, and the mixture warmed to R.T. and stirred for 46 h. The reaction mixture was concentrated in vacuo and 30 ml diethyl ether added to the residue. The solid was filtered off over Celite and the organic phase concentrated in vacuo. The residue was purified by silica gel chromatography using ethyl acetate/hexanes (3:7) to afford the product as a white solid (23%). Rf=0.44. 1HNMR (400 MHz, CDCl3): δ=5.73 (m, 1H), 4.93 (dd, 1H, 3JHH=17.0 Hz, 4JHH=1.5 Hz), 4.87 (d, 1H, 3JHH=10.3 Hz), 3.71 (m, 1H), 2.10 (t, 2H, 3JHH=7.8 Hz), 1.97 (q, 2H, 3JHH=7.3 Hz), 1.85 (m, 2H), 1.54-1.68 (m, 5H), 1.02-1.34 (m, 15H) ppm. 13CNMR (400 MHz, CDCl3): δ=172.2, 139.1, 114.1, 48.6, 48.0, 37.0, 34.0, 33.7, 33.2, 29.3, 29.2, 29.0, 28.8, 25.9, 25.7, 25.5, 25.0, 24.9 ppm. HRMS-ESI: Calculated [M-C2H2]+: 266.2358. found: 266.2474. The flask was purged with argon Dicyclohexycarbodiimide (2.2 mmol) was then add to the solution the mixture warmed to R.T. The reaction mixture was concentrated in vacuo and 30 ml diethyl ether added to the residue The solid was filtered off over Celite the organic phase concentrated in vacuo The residue was purified by silica gel chromatography

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

Procedure: An oven-dried 50 mL round bottom flask was charged with 3-aminoquinuclidine dihydrochloride (2 mmol), 10-undecenoic acid (2 mmol), N,N-dimethylaminopyridine (0.3 mmol), diisopropylethylamine (4 mmol), and dry DMF (15 mL). The flask was purged with argon and cooled to 0° C. in an ice bath. Dicyclohexycarbodiimide (2.2 mmol) was then add to the solution, the flask repurged with argon, and the mixture warmed to R.T. and stirred for 46 h. The reaction mixture was concentrated in vacuo and 30 ml diethyl ether added to the residue. The solid was filtered off over Celite and the organic phase concentrated in vacuo. The residue was purified by silica gel chromatography using ethyl acetate/hexanes (3:7) to afford the product as a white solid (23%). Rf=0.44. 1HNMR (400 MHz, CDCl3): δ=5.73 (m, 1H), 4.93 (dd, 1H, 3JHH=17.0 Hz, 4JHH=1.5 Hz), 4.87 (d, 1H, 3JHH=10.3 Hz), 3.71 (m, 1H), 2.10 (t, 2H, 3JHH=7.8 Hz), 1.97 (q, 2H, 3JHH=7.3 Hz), 1.85 (m, 2H), 1.54-1.68 (m, 5H), 1.02-1.34 (m, 15H) ppm. 13CNMR (400 MHz, CDCl3): δ=172.2, 139.1, 114.1, 48.6, 48.0, 37.0, 34.0, 33.7, 33.2, 29.3, 29.2, 29.0, 28.8, 25.9, 25.7, 25.5, 25.0, 24.9 ppm. HRMS-ESI: Calculated [M-C2H2]+: 266.2358. found: 266.2474. The flask was purged with argon Dicyclohexycarbodiimide (2.2 mmol) was then add to the solution the mixture warmed to R.T. The reaction mixture was concentrated in vacuo and 30 ml diethyl ether added to the residue The solid was filtered off over Celite the organic phase concentrated in vacuo The residue was purified by silica gel chromatography

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

Procedure: One equivalent of 2-nitrobenzyl alcohol (2.39 g, 15.65 mmol) was combined with one equivalent of undecylenic acid (2.88 g, 15.65 mmol) and 0.1 equivalents of DMAP and dissolved in 50 mL CH2Cl2. DCC (3.23 g, 15.65 mmol) was dissolved in 30 mL CH2Cl2 and slowly added to the mixture while stirring. A white precipitate slowly formed after about 5 minutes. The reaction mixture was stirred at room temperature overnight. The precipitate was filtered off by vacuum filtration and the filtrate was concentrated by rotovap. Silica gel column chromatography with CH2Cl2/MeOH (v/v 50:1) as eluent was used for purification. The product was dried over Na2SO4, solvent removed by rotovap, and dried under vacuum producing a yellow oil. Yield: 3.91 g (78.2%). 1H-NMR (CDCl3) δ (ppm): 8.1 (d, 1H, Ar), 7.7 (t, 1H, Ar), 7.6 (d, 1H, Ar), 7.5 (t, 1H, Ar), 5.8 (m, 1H, CH═CH2), 5.5 (s, 2H, CH2—O) 4.9 (dd, 2H, CH2═CH), 2.4 (t, 2H, CH2—C═O), 2.0 (q, 2H, CH2), 1.6 (m, 2H, CH2), 1.2 (m, 10H, CH2). 13C NMR (CDCl3) δ (ppm): 173.5, 147.9, 139.5, 134.1, 132.7, 129.4, 129.1, 125.4, 114.6, 63.2, 34.5, 34.2, 29.7, 29.6, 29.5, 29.4, 29.3, 25.3. MS (ESI): (M+H)+=320.30 (calc. 320.40). slowly added to the mixture A white precipitate slowly formed after about 5 minutes The reaction mixture was stirred at room temperature overnight The precipitate was filtered off by vacuum filtration the filtrate was concentrated by rotovap Silica gel column chromatography with CH2Cl2/MeOH (v/v 50:1) as eluent was used for purification The product was dried over Na2SO4, solvent removed by rotovap dried under vacuum producing a yellow oil

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

Procedure: To 1/2 N-potassium hydroxide/ethanol (200 mL) is added undecylenic acid (18.8 g, 0.102 mol) slowly dropwise at 0° C. with constant stirring. The volatile matter is then distilled off to give a crude product. This crude product is washed with acetone and heated in vacuo to provide potassium undecylenate of the following formula as white solid (8.88 g, yield 88%). The volatile matter is then distilled off to give a crude product This crude product is washed with acetone heated in vacuo

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

Procedure: Preferably, the cross metathesis reaction with acrylonitrile is carried out with a compound chosen from 9-decenoic acid or methyl 9-decenoate, resulting from the ethenolysis of oleic acid or methyl oleate, 10-undecenoic acid or methyl 10-undecenoate, resulting from the cracking of ricinoleic acid or methyl ricinoleate, oleic acid or methyl oleate, 9-octadecenedioic acid or methyl 9-octadecenedioate, resulting from the homometathesis or fermentation of oleic acid, erucic acid and methyl erucate, or 12-tridecenoic acid or methyl 12-tridecenoate, resulting from lesquerolic acid.

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

Procedure: Undecylenic acid (18.8 g, 0.102 mol) was added dropwise gradually to ½ N ethanolic solution of potassium hydroxide (200 mL) with stirring at 0° C. The volatile matter was distilled off under reduced pressure to give a crude product. The crude product was washed with acetone and heated under reduced pressure to give potassium undecylenate represented by the formula given below as a white solid (8.88 g, yield 88%). CH2═CH—(CH2)8—CO2−K+ The volatile matter was distilled off under reduced pressure to give a crude product The crude product was washed with acetone heated under reduced pressure

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

Procedure: (S)-3-(tert-Butoxycarbonylamino)glutarimide (a compound of formula XV wherein R1 is tert-butoxy; R2 is hydrogen, R3 and R4 together with the atoms to which they are attached are a six membered heterocyclic ring comprising five carbon atoms and N(H); R5 is hydrogen; and the center marked by * has the (S) configuration; 228 mg, 1 mmol) was dissolved in CH2Cl2 (2 mL) and the solution was cooled to 0° C. Trifluoroacetic acid (1 mL) was added dropwise, and the reaction was stirred for 1 hour. The reaction was then reduced in vacuo to give crude (S)-glutarimidyl-3-ammonium trifluoroacetate as a thick oil. This material was dissolved in DMF (1.5 mL) and (i-Pr)2NEt (1.5 mL), and the resulting solution was added to a solution of 10-undecenoic acid (1 mmol) and BOP (442 mg, 1 mmol) in DMF at 25° C. This reaction was stirred for 24 hours, and was then partitioned between EtOAc (30 mL) and 0.5 M HCl(aq) (20 mL). The organic layer was then washed twice more with 0.5 M HCl(aq) (20 mL), dried over Na2SO4 and reduced in vacuo to give a white solid which was chromatographed (SiO2/EtOAc) to give the title compound. to give crude (S)-glutarimidyl-3-ammonium trifluoroacetate as a thick oil This reaction was stirred for 24 hours was then partitioned between EtOAc (30 mL) and 0.5 M HCl(aq) (20 mL) The organic layer was then washed twice more with 0.5 M HCl(aq) (20 mL) dried over Na2SO4 to give a white solid which was chromatographed (SiO2/EtOAc)