Sodium Hydroxide → Ethyl (2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoate
Reaction equation
[CH2:1]1OCCOCCOCCOCCO[CH2:2]1.[OH-].[Na+].C([C:20]([CH2:33][CH3:34])(P(O)(O)=O)/[C:21](/[CH3:28])=[C:22](\CC)/[C:23]([O-:25])=[O:24])C.[CH3:35][C:36]([CH3:50])=[CH:37][CH2:38][CH2:39]/[C:40](/[CH3:49])=[CH:41]/[CH2:42][CH2:43]/[C:44](/[CH3:48])=C/C=O>C1(C)C=CC=CC=1>[CH3:28]/[C:21](/[CH:20]=[CH:33]/[CH:34]=[C:44](\[CH3:48])/[CH2:43][CH2:42]/[CH:41]=[C:40](\[CH3:49])/[CH2:39][CH2:38][CH:37]=[C:36]([CH3:35])[CH3:50])=[CH:22]\[C:23]([O:25][CH2:1][CH3:2])=[O:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
15-crown-5 (0.5 g, 0.1 equivalents, 2.27 mmol) was dissolved in 30 ml of toluene at room temperature, and added with 20 ml of 50% aqueous sodium hydroxide solution. To the solution, triethyl-3-methyl-4-phosphonocrotonate (7.87 g, 1.05 equivalents, 23.8 mmol) and then 5 ml toluene solution of farnesal (5.0 g, 22.7 ml) were added with stirring at 0° C. The mixture was stirred at room temperature for one hour. The organic and aqueous layers were separated, and the organic layer was washed with saturated ammonium chloride solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.4 g of the title compound (yield 98%, 2E:2Z=>99:1) as a yellow oil.
Workup
- stirringThe mixture was stirred at room temperature for one hour
- customThe organic and aqueous layers were separated
- washthe organic layer was washed with saturated ammonium chloride solution and saturated brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-42a2142c67ba406391e79b429d6051ef
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06984742B2
Reaction notes
Loading…