Sodium Hydroxide → ethyl(2E,4E,6E)-3,7,11-trimethyl-2,4,6,10-dodecatetraenoate
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](=[CH:38][CH2:39][CH2:40]/[C:41](=C/C=O)/[CH3:42])[CH3:37]>C1(C)C=CC=CC=1>[CH3:28]/[C:21](/[CH:20]=[CH:33]/[CH:34]=[C:41](\[CH3:42])/[CH2:40][CH2:39][CH:38]=[C:36]([CH3:37])[CH3:35])=[CH:22]\[C:23]([O:25][CH2:1][CH3:2])=[O:24]Participants
Conditions
- Temperature
- 0 °C
Procedure
15-crown-5 (0.9 g, 0.1 equivalents, 4.0 mmol) was dissolved in 50 ml of toluene at room temperature, and added with 32 ml of 50% aqueous sodium hydroxide solution. To the solution, triethyl-3-methyl-4-phosphonocrotonate (11.1 g, 1.05 equivalents, 42 mmol) and then 7 ml toluene solution of geranial (6.1 g, 40 mmol) were added under stirring at 0° C. The mixture was stirred at room temperature for 1.5 hours. 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 9.2 g of the title compound (yield 87%, 2E:2Z=93:7) as a yellow oil.
Workup
- stirringThe mixture was stirred at room temperature for 1.5 hours
- 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-98e6691ebbb24afc9643ea9b2839a1a7
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06984742B2
Reaction notes
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