Furan → HCID 573556, compound

HRID 1194125Notes

Reaction equation

HRID 1194125 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O.Cl[CH2:15][C:16]([O:18][C:19](=O)[CH2:20]Cl)=O.O1C=CC=C1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([C:16]1[O:18][CH:19]=[CH:20][CH:15]=1)=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 8029FuranHCID 10946Chloroacetic anhydrideHCID 5541918-Methoxy-8-oxooctanoic acid

Product 1

HCID 573556HCID 573556, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In 50 ml of toluene were dissolved 9.41 g (0.05 mole) of suberic acid monomethyl ester and 9.83 g (0.0575 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 6 hours. After completion of the reaction, the reaction solution was cooled and washed successively with of water, 5% aqueous sodium carbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure and the resulting concentrated residue was purified by silica gel-filled column chromatography to obtain 11 g of 2-(7-methoxycarbonyl-1-oxoheptyl)furan.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. washwashed successively with of water, 5% aqueous sodium carbonate solution and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting concentrated residue was purified by silica gel-
  7. additionfilled column chromatography

Sources & evidence

ORD record
ord-557ab431b336432d95f91da311cd583b
Source dataset
uspto-grants-1989_03
Patent number
US04812585

Reaction notes

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