Acetic Acid → Ethyl furan-3-propionate

HRID 611068Notes

Reaction equation

HRID 611068 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]/[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:2]1.O.NN.C(O)(=O)C.I([O-])(=O)(=O)=O.[Na+]>C(O)C.O.[Cu]=S>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:2]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 10103508(E)-ethyl 3-(furan-3-yl)acrylateHCID 23667635Sodium periodate

Product 1

HCID 92549Ethyl furan-3-propionate

Reagents, catalysts & solvents 3

HCID 14831Copper monosulfideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 8.186 g (49.26 mmol) of ethyl (E)-3-(3-furyl)acrylate, 24.7 g (493 mmol) of hydrazine monohydrate, 5 ml of acetic acid and 5 ml of saturated aqueous copper sulfide in 500 ml of ethanol, a solution of 52.7 g (246 mmol) of sodium periodate in 300 ml of water was added dropwise over a period of 1 hour, followed by stirring at room temperature for 1 day. The reaction mixture was extracted with ether 3 times. The combined organic layer was washed with dilute hydrochloric acid and then aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to yield the desired product.

Workup

  1. extractionThe reaction mixture was extracted with ether 3 times
  2. washThe combined organic layer was washed with dilute hydrochloric acid
  3. dry with materialaqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-69ab78185a7a44d58c2cb80c01a0cf3b
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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