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

HRID 31749

Reaktionsgleichung

Reaktionsgleichung von HRID 31749
[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

Komponenten

9

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 6342AcetonitrileLösungsmittel2×HCID 8471TriethylamineLösungsmittel2×HCID 65578Oxalyl chlorideLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-825e1fd4f92d46999bb219a64ae09682
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425557B2

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