(2Z,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-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:

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:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Chlorosuccinimide (0.66 g, 4.95 mmol) was dissolved in 20 ml of dry CH2Cl2 under a nitrogen atmosphere. The solution was cooled to -30° C. and 0.37 ml dimethyl sulphide (5 mmol) was added. The mixture was allowed to warm to 0° C. before it was cooled to -40° C. Then farnesol (1 g, 4.5 mmol) dissolved in 2.5 ml CH2 Cl2 was added dropwise to the mixture over a period of 3 minutes. The reaction mixture was warmed to 0.C in 1 h, at which temperature it was maintained for another hour. After 15 minutes of stirring at room temperature the reaction mixture was poured into a separatory funnel which contained 12.5 ml of cold saturated NaCl. The aqueous layer was extracted with two 10 ml portions of pentane. The organic layers were combined with an additional 10 ml of pentane and washed with two 5 ml portions of cold saturated NaCl. The organic layer was dried over MgSO4 and concentrated to dryness in vacuo. Compound (b) was thus obtained in a yield of 89%. to warm to 0° C. before it was cooled to -40° C was added dropwise to the mixture over a period of 3 minutes was maintained for another hour was poured into a separatory funnel which The aqueous layer was extracted with two 10 ml portions of pentane washed with two 5 ml portions of cold saturated NaCl The organic layer was dried over MgSO4 concentrated to dryness in vacuo

Conditions: temp:-65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of oxalyl chloride (4.68 g, 0.037 mol) in dry CH2Cl2 under argon atmosphere was cooled to -65° C. A solution of dimethyl sulfoxide (DMSO) (5.33 ml) in CH2Cl2 (17 ml) was added rapidly, dropwise, to the cooled oxalyl chloride solution. After stirring for 7 minutes at -65° C., a 10 ml CH2Cl2 solution of (E,E)-farnesol (7.0 g, 0.032 mol) was added over 10 minutes to the reaction solution at -65° C.: a precipitate formed upon the addition of approximately half of the farnesol solution. After the addition of the farnesol solution was completed, the reaction was stirred at -65° C. for 25 minutes, and then 22.4 ml (2 mol) of triethylamine was added over 10 minutes. After stirring for an additional 15 minutes at -65° C., the reaction was warmed to room temperature, and then diluted with water (~200 ml). The resulting aqueous layer was extracted several times with CH2Cl2. The combined organic layers were washed once with saturated aqueous NaCl solution, once with 1% HCl, once with 5% Na2CO3 solution and once with saturated aqueous NaCl solution. The resulting organic layer was dried over MgSO4 to give 7.05 g (100%) of a clear oil after filtration and solvent removal. After stirring for an additional 15 minutes at -65° C. the reaction was warmed to room temperature The resulting aqueous layer was extracted several times with CH2Cl2 The combined organic layers were washed once with saturated aqueous NaCl solution, once with 1% HCl, once with 5% Na2CO3 solution and once with saturated aqueous NaCl solution The resulting organic layer was dried over MgSO4