Furan → HCID 11367018, compound

HRID 1194133Notes

Reaction equation

HRID 1194133 reaction equation
[C:1]([OH:6])(=O)/[CH:2]=[CH:3]/[CH3:4].[O:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.ClCC(OC(=O)CCl)=O>C1(C)C=CC=CC=1>[C:8]([C:1]1[O:6][CH:4]=[CH:3][CH:2]=1)(=[O:7])/[CH:9]=[CH:10]/[CH3:11]

Participants

5

Reactant 3

HCID 8029FuranHCID 10946Chloroacetic anhydrideHCID 637090Crotonic Acid

Product 1

HCID 11367018HCID 11367018, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In 50 ml of toluene were dissolved 4.31 g (0.05 mole) of crotonic acid, 4.43 g (0.065 mole) of furan and 10.26 g (0.06 mole) of monochloroacetic anhydride. To the resulting solution was added 0.71 g of boron trifluoridediethyl ether complex and the resulting mixture was then stirred at 50° C. for 6.5 hours. After completion of the reaction, the reaction solution was cooled and washed successively with water, 5% aqueous sodium carbonate solution and water. The organic layer was concentrated under reduced pressure and the resulting concentrated residue was then purified by silica gel-filled column chromatography to obtain 2.8 g of 2-crotonylfuran.

Workup

  1. additionTo the resulting solution was added 0.71 g of boron trifluoridediethyl ether complex
  2. customAfter completion of the reaction
  3. temperaturethe reaction solution was cooled
  4. washwashed successively with water, 5% aqueous sodium carbonate solution and water
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting concentrated residue was then purified by silica gel-
  7. additionfilled column chromatography

Sources & evidence

ORD record
ord-6977f15e8c8e41baad50f01bc728259d
Source dataset
uspto-grants-1989_03
Patent number
US04812585

Reaction notes

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