Tetrahydrofuran → Ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate

HRID 2228596Notes

Reaction equation

HRID 2228596 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.C1COCC1.[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21]C([O-])=O.[K+].[Cl-].[Mg+2].[Cl-]>C(Cl)(=O)C(Cl)=O.CN(C=O)C.C(#N)C.C(N(CC)CC)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:10](=[O:12])[CH2:21][C:20]([O:26][CH2:27][CH3:28])=[O:25])=[CH:13][CH:14]=1

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 3446434Potassium ethyl malonateHCID 51387914-(Fur-2-yl)benzoic acidHCID 5360315Magnesium Chloride

Product 1

HCID 22142724Ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent2×HCID 65578Oxalyl chlorideSolvent2×

Procedure

The acid from Step 1 was converted to the acid chloride by refluxing in a mixture of oxalyl chloride (1.3 ml), THF (20 ml) and several drops of DMF. Small portions of oxalyl chloride were added until the reaction was homogeneous. Reflux continued for 0.5 hours, then the solvent was removed in vacuo to give the crude acid chloride. Meanwhile, potassium ethyl malonate (2.7 g) was reacted with anhydrous magnesium chloride (1.9 g) and triethylamine (2.21 ml) in dry acetonitrile (50 ml) at room temperature for 3 hours. Triethylamine (1 ml) was added, followed by addition of a solution of the acid chloride in acetonitrile. The mixture was then stirred overnight at room temperature, then concentrated to dryness. The residue was partitioned between toluene and 10% aqueous HCl. The organic layer was washed with 10% HCl and water, dried and was then concentrated to give crude ethyl 3-(4-(2-furyl)phenyl)-3-oxopropanoate as a solid.

Workup

  1. temperatureReflux
  2. customthe solvent was removed in vacuo
  3. customto give the crude acid chloride
  4. concentrationconcentrated to dryness
  5. customThe residue was partitioned between toluene and 10% aqueous HCl
  6. washThe organic layer was washed with 10% HCl and water
  7. customdried
  8. concentrationwas then concentrated

Sources & evidence

ORD record
ord-6b256f3155414e0089e4de9b4b5cfefa
Source dataset
uspto-grants-2002_07
Patent number
US06417185B1

Reaction notes

Loading…