10-chlorodec-1-ene

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

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10.0 g of 10-chloro-1-decene obtained in Example 1.(2) was iodized by reacting it with 25 g of sodium iodide in 2-butanone for 10 hours at 80° C. The resulting reaction mixture was then washed with water and dried, and the solvent was then removed. To the obtained iodide product were added 11.5 g of ethyl p-hydroxybenzoate and 9.6 g of potassium carbonate, and the mixture was refluxed in absolute ethanol for 15 hours. To the resulting reaction mixture was then added an aqueous potassium hydroxide solution containing 4.0 g of potassium hydroxide, and the mixture was further heated at 80° C. for 5 hours. After the reaction, the resulting reaction solution was made acid with hydrochloric acid and concentrated under reduced pressure. The resulting residue was suspended in water, and the insoluble material was corrected and dried to obtain 9.5 g of p-(9-decenyloxy)benozic acid. (Yield: 60%). for 10 hours at 80° C The resulting reaction mixture was then washed with water dried the solvent was then removed To the obtained iodide product were added 11.5 g of ethyl p-hydroxybenzoate and 9.6 g of potassium carbonate the mixture was refluxed in absolute ethanol for 15 hours To the resulting reaction mixture After the reaction the resulting reaction solution concentrated under reduced pressure dried to obtain 9.5 g of p-(9-decenyloxy)benozic acid

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

Procedure: 10 drops of pyridine was added to 26.0 g of 9-decene-1-ol and the mixture was placed in an eggplant type flask. Into the flask was then dropped 24.0 g of thionyl chloride while cooling with ice. After dropping thionyl chloride, reaction was carried out for 8.5 hours at 70° C. After the reaction, the resulting reaction solution was diluted with dichloromethane and was washed with an aqueous potassium hydroxide solution. The organic phase was dried over magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain 27.7 g of 10-chloro-1-decene. (Yield: 95%). the mixture was placed in an eggplant type flask while cooling with ice After the reaction the resulting reaction solution was washed with an aqueous potassium hydroxide solution The organic phase was dried over magnesium sulfate was then concentrated under reduced pressure The resulting residue was purified by column chromatography

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

Procedure: 10 drops of pyridine was added to 26.0 g of 9-decene-1-ol and the mixture was placed in an eggplant type flask. Into the flask was then dropped 24.0 g of thionyl chloride while cooling with ice. After dropping thionyl chloride, reaction was carried out for 8.5 hours at 70° C. After the reaction, the resulting reaction solution was diluted with dichloromethane and was washed with an aqueous potassium hydroxide solution. The organic phase was dried over magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain 27.7 g of 10-chloro-1-decene. (Yield: 95%). the mixture was placed in an eggplant type flask while cooling with ice After the reaction the resulting reaction solution was washed with an aqueous potassium hydroxide solution The organic phase was dried over magnesium sulfate was then concentrated under reduced pressure The resulting residue was purified by column chromatography

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

Procedure: 10 drops of pyridine was added to 26.0 g of 9-decene-1-ol and the mixture was placed in an eggplant type flask. Into the flask was then dropped 24.0 g of thionyl chloride while cooling with ice. After dropping thionyl chloride, reaction was carried out for 8.5 hours at 70° C. After the reaction, the resulting reaction solution was diluted with dichloromethane and was washed with an aqueous potassium hydroxide solution. The organic phase was dried over magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain 27.7 g of 10-chloro-1-decene. (Yield: 95%). the mixture was placed in an eggplant type flask while cooling with ice After the reaction the resulting reaction solution was washed with an aqueous potassium hydroxide solution The organic phase was dried over magnesium sulfate was then concentrated under reduced pressure The resulting residue was purified by column chromatography

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

Procedure: To a flame-dried round-bottomed flask, evacuated and backfilled with nitrogen (3×), was added 10-chlorodecene (1 equiv, 16 mmol, 2.79 g), methyl acrylate (25 equiv, 395 mmol, 36 mL), and CH2Cl2 (140 mL). Grubbs 2 catalyst (0.031 equiv, 0.48 mmol, 416 mg) was dissolved in CH2Cl2 (15 mL) and added to the reaction mixture in one portion. The reaction was stirred for 4 h, concentrated in vacuo, and purified by flash column chromatography (3% EtOAc/Hex) to afford (E)-methyl 11-chloroundec-2-enoate (3.14 g, 13.6 mmol, 85%). TLC Rf=0.30 (5% EtOAc/Hex); 1HNMR (300 MHz): δ 6.99 (dt, 1H, J=15.6, 7.0 Hz), 5.84 (dt, 1H, J=15.7, 1.5 Hz), 3.75 (s, 3H), 3.55 (t, 2H, J=6.8 Hz), 2.22 (qd, 2H, J=7.3, 1.4 Hz), 1.72-1.85 (m, 2H), 1.26-1.55 (10H); 13CNMR (75 MHz): δ 167.2, 149.6, 120.9, 51.4, 45.1, 32.6, 32.2, 29.2, 29.0, 28.7, 27.9, 26.8; FTIR: 2928, 2856, 1722, 1657, 1435, 1270, 1195, 1174, 1041, 979, 720 cm−1; HRMS-ESI: calc. for C12H21ClNaO2 (M+Na)+: 255.1128. found: 255.1118. To a flame-dried round-bottomed flask, evacuated added to the reaction mixture in one portion concentrated in vacuo purified by flash column chromatography (3% EtOAc/Hex)

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

Procedure: To a flame-dried round-bottomed flask was added PPh3 (1.1 equiv, 27.5 mmol, 7.21 g) and THF (65 mL). N-chlorosuccinimide (1.1 equiv, 27.5 mmol, 3.67 g) was dissolved in THF (50 mL) and added dropwise. The mixture was stirred for 5 min, and 9-decen-1-ol (1 equiv, 25 mmol, 3.91 g) was added dropwise in THF (30 mL). After 9 h, the volatile components of the reaction were evaporated and hexanes (100 mL) and H2O (50 mL) were added. The liquid was decanted and the resulting solid was washed with hexanes. The aqueous layer was collected and extracted with hexanes (2×50 mL). The combined organic layers were washed sequentially with bleach (30 mL) and brine (50 mL). The crude product was filtered through a pad of silica (which was washed with ˜400 mL of hexanes) and concentration in vacuo to afford 10-chlorodecene (3.48 g, 20 mmol, 80%), which was deemed pure by NMR and used without further purification. TLC Rf=0.87 (5% EtOAc/Hex); 1HNMR (400 MHz): δ 5.84 (ddt, 1H, J=17.4, 10.3, 6.7 Hz), 5.02 (ddd, 1H, J=17.4, 2.0, 3.6 Hz), 4.93-4.98 (m, 1H), 3.56 (t, 2H, J=6.5 Hz), 2.02-2.12 (m, 2H), 1.74-1.84 (2H), 1.27-1.50 (10H); 13CNMR (100 MHz): δ 139.2, 114.2, 45.2, 33.8, 32.7, 29.3, 29.0, 28.88, 28.85, 26.88. added dropwise After 9 h the volatile components of the reaction were evaporated hexanes (100 mL) and H2O (50 mL) were added The liquid was decanted the resulting solid was washed with hexanes The aqueous layer was collected extracted with hexanes (2×50 mL) The combined organic layers were washed sequentially with bleach (30 mL) and brine (50 mL) The crude product was filtered through a pad of silica (which was washed with ˜400 mL of hexanes) and concentration in vacuo

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

Procedure: To 26.0 g of 9-decene-1-ol was added 10-drops of pyridine and the mixture was placed into an eggplant flask. To the eggplant flask was added dropwise 24.0 g of thionyl chloride during cooling with ice. After dropping, the mixture was reacted for 8.5 hours at 70° C. After the conclusion of the reaction, the reaction product was diluted with dichloromethane and then washed with an aqueous potassium carbonate solution. The reaction solution was then dried over magnesium sulfate and subsequently concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain 27.7 g of 10-chloro-1-decene. (Yield: 95%) the mixture was placed into an eggplant flask during cooling with ice the mixture was reacted for 8.5 hours at 70° C After the conclusion of the reaction washed with an aqueous potassium carbonate solution The reaction solution was then dried over magnesium sulfate subsequently concentrated under reduced pressure The resulting residue was purified by column chromatography