Water → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienamide

HRID 1761774Notes

Reaction equation

HRID 1761774 reaction equation
[CH2:1]([CH2:11][C:12](=O)[CH3:13])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C([N:17](CC)[C:18](=[O:24])[CH2:19]P(O)(O)=O)C.[H-].[Na+].O>C(COC)OC>[CH3:13]/[C:12](/[CH2:11][CH2:1]/[CH:2]=[C:3](\[CH3:4])/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])=[CH:19]\[C:18]([NH2:17])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1549778GeranylacetoneHCID 18756985[(Diethylcarbamoyl)methyl]phosphonic acid

Product 1

HCID 5275515(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 5 g of E-geranylacetone in 90 ml of dimethoxyethane is treated at -20° with 25.1 g of phosphonoacetamide diethyl ester and 1.86 g of 50% sodium hydride dispersion in mineral oil. The reaction mixture is stirred at room temperature for 3.5 hours under argon. After the addition of water the mixture is extracted with ethyl acetate. The organic phase is dried and freed from solvent. Crystallization of the (2E/Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienamide (4:1 2E/Z mixture), which remains behind as the residue, from hexane gives white crystals, m.p. 51°-52.5°. This material is recrystallized a further twice from hexane, there being obtained pure (E,E)-3,7,11-trimethyl-2,6,10-dodecatrienamide as a white crystalline material of m.p. 53°-53.5°.

Workup

  1. extractionis extracted with ethyl acetate
  2. customThe organic phase is dried
  3. customCrystallization of the (2E/Z,6E)-3,7,11-trimethyl-2,6,10-dodecatrienamide (4:1 2E/Z mixture), which
  4. customgives white crystals, m.p. 51°-52.5°
  5. customThis material is recrystallized a further twice from hexane, there

Sources & evidence

ORD record
ord-a37d9dfda92f48a6954e1063cc370a1c
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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