Allyl Alcohol → 3-(2-Chlorophenyl)propanal

HRID 1910679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910679
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH2:9]([OH:12])[CH:10]=[CH2:11].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][CH2:10][CH:9]=[O:12]

Komponenten

8

Edukt 3

HCID 7858Allyl AlcoholHCID 119931-Chloro-2-iodobenzeneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 218597263-(2-Chlorophenyl)propanalAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

2-Chloro-iodobenzene (700 mg), allyl alcohol (256 mg, 1.5 eq.), palladium acetate (13 mg, 0.02 eq), sodium bicarbonate (616 mg, 2.5 eq), and tetrabutylammonium chloride (816 mg, 1 eq) were mixed together in anhydrous DMF (12 mL). The mixture was stirred at 30° C. for 24 h, then diluted with water. The crude mixture was extracted into EtOAc 3×, and the organic layer was washed with water twice, then brine, and then dried over sodium sulfate, and concentrated. The residue was purified by chromatography (gradient: 88:12 hexanes:EtOAc to 1:1 hexanes:EtOAc) delivering the product (200 mg, 40% yield). 1H-NMR (300 MHz, CDCl3) δ 9.80 (s, 1H), 7.38-7.30 (m, 1H), 7.28-7.10 (m, 3H), 3.10-3.02 (m, 2H), 2.84-2.68 (m, 2H).

Aufarbeitung

  1. extractionThe crude mixture was extracted into EtOAc 3×
  2. washthe organic layer was washed with water twice
  3. dry with materialbrine, and then dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (gradient: 88:12 hexanes:EtOAc to 1:1 hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-881596b5f9d84ca2bd97231720d84a1e
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604023B2

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