undec-10-en-1-ol

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:

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: A mixture of 10-undecene-1-ol (5.00 g, 29.36 mmol, 1 equiv), triphenylphosphine (7.70 g, 29.36 mmol, 1 equiv) and phthalimide (4.32 g, 29.36 mmol, 1 equiv) in dry tetrahydrofuran (THF, 30 mL) was stirred vigorously under argon. Diethyl azodicarboxylate (DEAD, 5.11 g, 29.36 mmol, 1 equiv) was diluted with THF (12 mL) and added dropwise by syringe. After the addition, the reaction was stirred at room temperature for 4 hours. The solvent was evaporated under vacuum and ether (30 mL) was added to precipitate the triphenylphosphine oxide and hydrazine dicarboxylate which were removed by filtration. The precipitate was rinsed with ether (2×30 mL) and the combined filtrates were evaporated to afford a yellow solid. The yellow solid was triturated with warm hexanes (3×50 mL) and filtered. The combined hexanes were evaporated to give 1-phthalimidylundec-10-ene as a yellow wax. added dropwise by syringe After the addition the reaction was stirred at room temperature for 4 hours The solvent was evaporated under vacuum and ether (30 mL) was added to precipitate the triphenylphosphine oxide and hydrazine dicarboxylate which were removed by filtration The precipitate was rinsed with ether (2×30 mL) the combined filtrates were evaporated to afford a yellow solid The yellow solid was triturated with warm hexanes (3×50 mL) filtered The combined hexanes were evaporated

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

Procedure: Compound XXXI was prepared as described in Scheme I from 10-undecen-1-ol, 1, by a three step procedure in an overall yield of 31%. Alkylation of phthalimide with alkanol, 1, under Mitsunobu conditions, followed by reaction with hydrazine gave 1-aminoundec-10-ene, 2, in 66% yield. The amine was derivatized with O-acetylsalicyloyl chloride and the resulting alkene, 3, was oxidized to the acid using potassium permanganate. Removal of the acetate, followed by acid precipitation provided compound XXXI in 47% yield based on amine 2. ##STR65##

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

Procedure: A suspension of [1,1′;4′,1″]terphenyl-4,4″-dicarboxylic acid (6.37 g, 20 mmol) in 100 ml of thionyl chloride was heated at reflux for 12 h then thionyl chloride was evaporated by azeotropic distillation. The crude yellow residue obtained therefrom was mixed with 10-undecen-1-ol (7.49 g, 44 mmol) in dichloromethane (300 ml) and triethylamine (8.9 g, 88 mmol) was added dropwise to the resulting mixture. The reaction mixture was stirred at 6 h at room temperature, then poured into water (300 ml) and extracted with dichloromethane (2×400 ml). The combined organic extracts were washed with saturated NaCl solution (500 ml), dried over magnesium sulphate, filtered and evaporated to dryness to give a brownish residue which was recrystallised from acetone/dichlorometane: 9/1 to afford pure [1,1′;4′,1″]terphenyl-4,4″-dicarboxylic acid diundec-10-enyl ester as white crystalline material. Yield 8.97 g. was heated at reflux for 12 h thionyl chloride was evaporated by azeotropic distillation The crude yellow residue obtained was added dropwise to the resulting mixture extracted with dichloromethane (2×400 ml) The combined organic extracts were washed with saturated NaCl solution (500 ml) dried over magnesium sulphate filtered evaporated to dryness to give a brownish residue which was recrystallised from acetone/dichlorometane

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

Procedure: C4F9(CH2)11OAcr was prepared essentially as described above starting with the AIBN catalyzed addition of C4F9I to CH2═CH(CH2)9OH. The resulting iodohydrin was reduced with zinc in ethyl alcohol to give the desired C4F9(CH2)11OH and olefinic products in about an 80:20 ratio as follows.

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

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