Propanal → 1,3-Diphenylhexane-1,4-dione

HRID 2235822

Reaktionsgleichung

Reaktionsgleichung von HRID 2235822
[CH:1]1[CH:2]=[CH:3][C:4](/[CH:7]=[CH:8]/[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:5][CH:6]=1.[CH:17](=[O:20])[CH2:18][CH3:19].C(N(CC)CC)C>[Br-].C([N+]1C(C)=C(CCO)SC=1)C.C(O)C>[C:11]1([C:9](=[O:10])[CH2:8][CH:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:17](=[O:20])[CH2:18][CH3:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 527PropanalHCID 8471TriethylamineHCID 637760Chalcone

Produkt 1

HCID 127547531,3-Diphenylhexane-1,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of (E)-1,3-diphenyl-propenone (1.042 g; 5.00 mmol), propionaldehyde (0.40 mL; 5.6 mmol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (126 mg; 0.500 mmol) and triethyl-amine (0.42 mL; 3.0 mmol) in absolute ethanol (3.0 mL) was degassed then heated at 70° C. for 25 h. After an additional 1.5 h at 80° C., the organic volatiles were removed on a rotary evaporator. EtOAc (25 mL) was added and the solution washed with water (3×5 mL) and satd NaCl (2×5 mL); then dried (MgSO4), filtered through silica and washed through with EtOAc. Crude product was adsorbed onto silica (2.0 g) then purified by MPLC (40 g of silica using a 0→20% EtOAc in hexanes gradient). Pure product was obtained as a clear, pale tan liquid (760 mg; 57%). 1H NMR (CDCl3) δ 7.96 (m, 2H), 7.56 (m, 1H), 7.45 (m, 2H), 7.38-7.26 (m, 5H), 4.43 (dd, J=3.4, 10.2 Hz, 1H), 4.05 (dd, J=10.4, 18.0 Hz, 1H), 3.14 (dd, J=3.8, 18.2 Hz, 1H), 2.65 (m, 1H), 2.53 (m, 1H), 1.02 (t(app), J=7.2 Hz, 3H).

Aufarbeitung

  1. customwas degassed
  2. customthe organic volatiles were removed on a rotary evaporator
  3. additionEtOAc (25 mL) was added
  4. washthe solution washed with water (3×5 mL) and satd NaCl (2×5 mL)
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered through silica
  7. washwashed through with EtOAc
  8. customthen purified by MPLC (40 g of silica using a 0→20% EtOAc in hexanes gradient)
  9. customPure product was obtained as a clear, pale tan liquid (760 mg; 57%)

Quellen und Nachweise

ORD-Eintrag
ord-23fa8a4a39b0464ca7cb33f39b659fdb
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714022B2

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