Trifluoroacetic anhydride → HCID 86738421, compound

HRID 1156263Notes

Reaction equation

HRID 1156263 reaction equation
[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](O)=[O:19].F[C:22](F)(F)[C:23]([O:25][C:26](=O)[C:27](F)(F)F)=O.[O:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[C:39]([CH3:46])=[CH:40][C:41]([O:43]CC)=[O:42].C(=O)([O-])[O-].[Na+].[Na+]>Cl(O)(=O)(=O)=O.CCOCC>[CH3:22][CH2:23][O:25][CH2:26][CH3:27].[O:19]=[C:18]([C:38]1[O:34][C:35]([C:39]([CH3:46])=[CH:40][C:41]([O-:43])=[O:42])=[CH:36][CH:37]=1)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH:7]=[CH:6][CH2:5][CH:4]=[CH:3][CH2:2][CH3:1]

Participants

7

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 5280934Linolenic AcidHCID 54533361HCID 54533361, compound

Product 1

HCID 86738421HCID 86738421, compound

Reagents, catalysts & solvents 2

HCID 24247Perchloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 13.0 g (0.05 mole) of linolenic acid and 12.6 g (0.06 mole) of trifluoroacetic anhydride is stirred at room temperature for 1 hour. To the mixture 9.0 g (0.05 mole) of ethyl 3-(2-furanyl)-2-butenoate is added and the mixture is cooled and stirred at -10° C. To the mixture 5 drops of 70% perchloric acid is added and the mixture stirred at 0° C. for 3 hours. The mixture is diluted with 200 ml of ether and combined with 200 ml of saturated aqueous sodium carbonate. The layers are separated and the ether layer is washed with water, brine and evaporated to dryness. The residue is distilled under high vacuum to give ether 3-[5-(1-oxo-9,12,15-octadecatrienyl)-2-furanyl]-2-butenoate, which ester is dissolved in 300 ml of anhydrous ethanol and the solution is cooled on an ice-bath. To the mixture 14.6 g (0.2 mole) of diethylamine is added and the mixture allowed to warm up to room temperature and stand for 3 days. The reaction mixture is evaporated to dryness to give N,N-diethyl-3-[5-(1-oxo-9,12,14-octadecatrienyl)-2-furanyl]-2-butenamide.

Workup

  1. temperaturethe mixture is cooled
  2. stirringstirred at -10° C
  3. stirringthe mixture stirred at 0° C. for 3 hours
  4. customThe layers are separated
  5. washthe ether layer is washed with water, brine
  6. customevaporated to dryness
  7. distillationThe residue is distilled under high vacuum

Sources & evidence

ORD record
ord-a3fdb34a729c4fd086e459c959f6bdc7
Source dataset
uspto-grants-1982_06
Patent number
US04335098

Reaction notes

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