Benzaldehyde → Dalosirvat

HRID 623795

Reaktionsgleichung

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

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

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

Quellen und Nachweise

ORD-Eintrag: ord-4a814f52ad9f4935a1248735ec214dc4
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09303010B2

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