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Sodium Hydroxide → Ethyl (2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoate

HRID 1611060
Notes
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Reaction equation

HRID 1611060 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 3633615-Crown-5HCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienalHCID 86584517Triethyl-3-methyl-4-phosphonocrotonate

Product 1

HCID 11984134Ethyl (2E,4E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,10,14-pentaenoateYield 986.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

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

  1. stirringThe mixture was stirred at room temperature for one hour
  2. customThe organic and aqueous layers were separated
  3. washthe organic layer was washed with saturated ammonium chloride solution and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-42a2142c67ba406391e79b429d6051ef
Source dataset
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06984742B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes