Triacetoxyperiodinane → 2-(1-Methoxycycloheptyl)-5-(trifluoromethyl)benzaldehyde

HRID 2075077

Reaktionsgleichung

Reaktionsgleichung von HRID 2075077
[CH3:1][O:2][C:3]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[CH2:20][OH:21])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:11]=2[CH:20]=[O:21])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

5

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 58968719(2-(1-Methoxycycloheptyl)-5-(trifluoromethyl)phenyl)methanol

Produkt 1

HCID 589686662-(1-Methoxycycloheptyl)-5-(trifluoromethyl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2-(1-methoxycycloheptyl)-5-(trifluoromethyl)phenyl)methanol (167 mg; 0.552 mmol) in methylene chloride (3.0 mL) was added Dess-Martin reagent (290 mg; 0.683 mmol). Reaction was stirred at room temperature for 5 hours. The reaction was diluted with ethyl acetate and quenched with aqueous 1N sodium hydroxide. After partitioning off the aqueous layer, the organic layer was washed with water and brine. It was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified over a Bakerbond 1 g silica cartridge (Mallinkrodt Baker Inc. Phillipsburg, N.J.) (eluted with 0-5% heptane) to yield 167 mg of a cloudy oil. 1H NMR (400 MHz, CDCl3) δ ppm 10.91 (s, 1H), 811 (d, J=2.07 Hz, 1H), 7.73 (dd, J=8.71, 8.30 Hz, 1H), 7.48 (d, J=7.88 Hz, 1H), 2.96 (s, 3H), 2.25 (m, 2H), 2.09 (m, 2H), 1.94-1.57 (m, 8H).

Aufarbeitung

  1. customReaction
  2. customquenched with aqueous 1N sodium hydroxide
  3. customAfter partitioning off the aqueous layer
  4. washthe organic layer was washed with water and brine
  5. dry with materialIt was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified over a Bakerbond 1 g silica cartridge (Mallinkrodt Baker Inc. Phillipsburg, N.J.) (eluted with 0-5% heptane)
  8. customto yield 167 mg of a cloudy oil

Quellen und Nachweise

ORD-Eintrag
ord-ce32c94f845c4b6d98cb900181ac5558
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919506B2

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