Triethylamine → 5-(4'-Ethoxycarbonyloxy-3'methoxyphenyl)pentadienoic acid geranylamide

HRID 654342Notes

Reaction equation

HRID 654342 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH:10]=[CH:11][C:12]([OH:14])=O)=[CH:4][C:3]=1[O:15][CH3:16].C([N:19]([CH2:22][CH3:23])CC)C.[C:24](Cl)(=[O:28])[O:25][CH2:26][CH3:27]>C(Cl)Cl>[CH2:22]([NH:19][C:12](=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][C:24]([O:25][CH2:26][CH3:27])=[O:28])=[C:3]([O:15][CH3:16])[CH:4]=1)/[CH:23]=[C:11](/[CH2:10][CH2:9][CH:8]=[C:5]([CH3:6])[CH3:4])\[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 542168095-(4-Hydroxy-3-methoxyphenyl)penta-2,4-dienoic acid

Product 1

HCID 867459905-(4'-Ethoxycarbonyloxy-3'methoxyphenyl)pentadienoic acid geranylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

Separately, 2.33 g of 5-(4'-hydroxy-3'-methoxyphenyl)pentadienoic acid is suspended in 50 ml of methylene chloride under an argon atmosphere. To the suspension cooled to -10° C. are added 2.95 ml of triethylamine and 2.03 ml of ethyl chlorocarbonate. To the mixture, after stirred for 30 min., is added a suspension of the geranylamine-hydrazide mixture in methylene chloride. The resulting mixture is stirred at -10° C. to 0° C. for 4 hours. The reaction mixture is filtered, and precipitates are washed with methylene chloride. Combined filtrate and washing are washed successively with water and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure, and the residue is subjected to column chromatography on silica gel. From the fraction eluted with chloroform is obtained 2.61 g of 5-(4'-ethoxycarbonyloxy-3'methoxyphenyl)pentadienoic acid geranylamide.

Workup

  1. additionis added
  2. stirringThe resulting mixture is stirred at -10° C. to 0° C. for 4 hours
  3. filtrationThe reaction mixture is filtered
  4. customprecipitates
  5. washare washed with methylene chloride
  6. washCombined filtrate and washing
  7. washare washed successively with water and saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent is distilled off under reduced pressure
  10. washFrom the fraction eluted with chloroform

Sources & evidence

ORD record
ord-210e7e0b83344971938b661da57056c9
Source dataset
uspto-grants-1992_07
Patent number
US05130483

Reaction notes

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