Furan → HCID 573556, compound

HRID 1194134Notes

Reaction equation

HRID 1194134 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 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °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 1.0 g of boron trifluoride-acetic acid complex and the resulting mixture was then stirred at 60° 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 10.1 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 5% aqueous sodium carbonate solution and water
  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-6ac7bb11abc54a97a4a7d7098ce6bc73
Source dataset
uspto-grants-1989_03
Patent number
US04812585

Reaction notes

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