Reaction #2439930

Reaction equation

pentane

(5Z,8Z)-1,5,8-undecatrien-3-ol

hexamethylphosphoric triamide

methyl(triphenoxy)phosphonium iodine

→

(3E,5E,8Z)-1,3,5,8-undecatetraene

Yield 20.0%

(3E,5Z,8Z)-1,3,5,8-undecatetraene

Yield 20.0%

Solvents

diethyl ether

Conditions

Workup

1. 1
   Extractionby extracting with pentane
2. 2
   WashAfter the organic layer was washed with a saturated aqueous sodium chloride solution, it
3. 3
   Dryingwas dried over anhydrous magnesium sulfate
4. 4
   OtherAfter evaporation of the solvent
5. 5
   Otherto give 2.0 g (yield: 74%) of a crude product

Procedure

(5Z,8Z)-1,5,8-undecatrien-3-ol (3.0 g, 18.1 mmol), 60 ml of hexamethylphosphoric triamide (HMPTA) and 16.4 g (36.2 mmol) of methyl(triphenoxy)phosphonium iodine (MTPI) were added to a reactor under a nitrogen atmosphere followed by stirring at room temperature for 3 hours and at 50° C. for 1 hour. The reaction was stopped by addition of 50 ml of ice water followed by extracting with pentane. After the organic layer was washed with a saturated aqueous sodium chloride solution, it was dried over anhydrous magnesium sulfate. After evaporation of the solvent, the resulting residue was subjected to a chromatographic treatment using pentane to give 2.0 g (yield: 74%) of a crude product. The resultant crude product (0.5 g, 3.37 mmol) was further purified by a chromatography using pentane and diethyl ether to give 0.05 g (yield: 20%) of (3E,5Z,8Z)-1,3,5,8-undecatetraene and 0.05 g (yield: 20%) of (3E,5E,8Z)-1,3,5,8-undecatetraene.

Source