Furan → HCID 14473413, compound

HRID 1194132Notes

Reaction equation

HRID 1194132 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O.[O:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1.ClC(Cl)C(OC(=O)C(Cl)Cl)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([C:12]1[O:11][CH:15]=[CH:14][CH:13]=1)=[O:10]

Participants

5

Reactant 3

HCID 8029FuranHCID 77772Acetic acid, 2,2-dichloro-, 1,1'-anhydrideHCID 150030106-Methoxyhexanoic acid

Product 1

HCID 14473413HCID 14473413, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In 50 ml of toluene were dissolved 7.31 g (0.05 mole) of 6-methoxyhexanoic acid, 4.43 g (0.065 mole) of furan and 14.39 g (0.06 mole) of dichloroacetic anhydride. To the resulting solution was added 0.71 g of boron trifluoride-diethyl ether complex and the resulting mixture was then stirred at 50° C. for 3 hours. After completion of the reaction, the reaction solution was cooled and washed successively with 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 8.83 g of 2-(6-methoxyhexanoyl)furan.

Workup

  1. additionTo the resulting solution was added 0.71 g of boron trifluoride-diethyl ether complex
  2. customAfter completion of the reaction
  3. temperaturethe reaction solution was cooled
  4. washwashed successively with 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-812cf73aa1754b79b8fd5005e8ecd010
Source dataset
uspto-grants-1989_03
Patent number
US04812585

Reaction notes

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