Furan → 2-Heptanoylfuran

HRID 1194126Notes

Reaction equation

HRID 1194126 reaction equation
[C:1](O)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].ClCC(OC(=O)CCl)=O.[O:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1>C1(C)C=CC=CC=1>[C:1]([C:20]1[O:19][CH:23]=[CH:22][CH:21]=1)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 8029FuranHCID 8094Heptanoic AcidHCID 10946Chloroacetic anhydride

Product 1

HCID 2313272-HeptanoylfuranYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In 50 ml of toluene were dissolved 6.51 g (0.05 mole) of heptanoic acid and 10.26 g (0.06 mole) of monochloroacetic anhydride. To the resulting solution were added 4.43 g (0.065 mole) of furan and 0.71 g of boron trifluoride-diethyl ether complex and the resulting mixture was then stirred at 50° C. for 5.5 hours. After completion of the reaction, the reaction solution was cooled and washed with 5% aqueous sodium carbonate solution and water in this order. The organic layer was concentrated under reduced pressure and the resulting concentrated residue was then purified by silica gel-filled column chromatography to obtain 8.2 g of 2-heptanoylfuran.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. washwashed with 5% aqueous sodium carbonate solution and water in this order
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resulting concentrated residue was then purified by silica gel-
  6. additionfilled column chromatography

Sources & evidence

ORD record
ord-6b2e543fda304bac8fed2b159443fc99
Source dataset
uspto-grants-1989_03
Patent number
US04812585

Reaction notes

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