Triacetoxyperiodinane → 3-(Furan-2-yl)propanal

HRID 253622

Reaktionsgleichung

Reaktionsgleichung von HRID 253622
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][OH:9].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH:8]=[O:9]

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 2271783-(Furan-2-yl)propan-1-ol

Produkt 1

HCID 117685663-(Furan-2-yl)propanalAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product from Example 50A (2.0 g, 15.9 mmol) in CH2Cl2 (50 mL) was treated with Dess-Martin periodinane (8.1 g, 19.2 mmol) in portions. The mixture was stirred at rt for 2 hrs, quenched with saturated NaS2O3, and the mixture was extracted with CH2Cl2. The CH2Cl2 layer was washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated. The resulting residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 1.44 g (73%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 2.80 (t, J=8.24, 6.41 Hz, 2H) 2.98 (t, J=7.32 Hz, 2H) 6.02 (d, J=3.97 Hz, 1H) 6.19-6.36 (m, 1H) 7.28-7.33 (m, 1H) 9.82 (s, 1H).

Aufarbeitung

  1. customquenched with saturated NaS2O3
  2. extractionthe mixture was extracted with CH2Cl2
  3. washThe CH2Cl2 layer was washed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-44135ade48c7444d81d80b32cb9ee5d4
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872033B2

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