1,4-Dioxane → Ketone, 3-furyl phenyl

HRID 48046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48046
[O:1]1[CH2:6][CH2:5]O[CH2:3][CH2:2]1.Br[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12].C([Sn](CCCC)(CCCC)C1OC=CC=1)CCC.[F-].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[O:1]1[CH:6]=[CH:5][CH:3]=[C:2]1[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12]

Komponenten

7

Edukt 4

HCID 312751,4-DioxaneHCID 765833-BromobenzaldehydeHCID 522689Potassium FluorideHCID 43936882-(Tributylstannyl)furan

Produkt 1

HCID 201640Ketone, 3-furyl phenylAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ex-592A) To a dioxane (20 mL) solution of 3-bromobenzaldehyde (0.63 mL, 5.4 mmol) was added 2-(tributylstannyl)furan (1.89 mL, 6.00 mL) and Pd(PPh3)2Cl2 (0.21 g, 0.30 mmol). The mixture was heated to reflux under argon for 1.5 h. The cooled mixture was poured into a mixture of saturated KF and ethyl acetate and stirred 18 h. The slurry was filtered through celite. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane gave 0.80 g (86%) of the desired 3-(2-furanyl)benzaldehyde product as an yellow oil which solidified upon standing. MS: m/z=173.1 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux under argon for 1.5 h
  3. filtrationThe slurry was filtered through celite
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to an oil
  8. customPurification by flash chromatography on silica gel eluting with 5% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4dddcd75d09d4a3bb894f693423fc15a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699898B2

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