Benzaldehyde → Dalosirvat

HRID 469901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469901
C(N(CC)CC)C.[CH:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O:16]1[CH2:21][CH2:20][O:19][C:18]2[CH:22]=[C:23]([C:26](=[O:32])[CH2:27][CH2:28]N(C)C)[CH:24]=[CH:25][C:17]1=2>O1CCOCC1.[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[O:16]1[CH2:21][CH2:20][O:19][C:18]2[CH:22]=[C:23]([C:26](=[O:32])[CH2:27][CH2:28][C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:15])[CH:24]=[CH:25][C:17]1=2

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 28250181-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-(dimethylamino)propan-1-one

Produkt 1

HCID 56837361DalosirvatAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideKatalysatorHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Triethylamine (3.61 mmol) and benzaldehyde (4.3 mmol) in dry dioxane (10 mL) was added to a solution of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(dimethylamino)propan-1-one (XVI) (5.4 mmol) and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (0.43 mmol) in dioxane heated at 95° C. under nitrogen. The solution was further heated overnight at 95° C. The solution was cooled and excess solvent was evaporated under vacuum. The residue was partitioned between CH2Cl2 and water. The organic phase was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate in hexane gradient to yield 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-phenylbutane-1,4-dione 1 as a white solid (12% yield). 1H NMR (DMSO-d6, 400 MHz): δ ppm 3.33-3.37 (m, 4H), 4.29 (m, 2H), 4.34 (m, 2H), 6.98 (m, 1H), 7.48 (m, 1H), 7.55 (m, 3H), 7.64 (m, 1H), 8.00-8.02 (m, 2H); ESIMS found C18H16O4 m/z 297 (M+H).

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customexcess solvent was evaporated under vacuum
  3. customThe residue was partitioned between CH2Cl2 and water
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate in hexane gradient

Quellen und Nachweise

ORD-Eintrag
ord-9c27f16ec18348e1b1ec262903d26976
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629176B1

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