Water → Usaf DO-2

HRID 591157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591157
[C:1]1([CH2:7][CH:8]([C:10]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)SCCCS2)[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(#N)C.[OH2:25]>C(OCC)(=O)C>[OH:9][CH:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:25]

Komponenten

5

Edukt 3

HCID 962WaterHCID 6342AcetonitrileHCID 222719962-Phenyl-1-(2-phenyl-[1,3]-dithian-2-yl)-ethanol

Produkt 1

HCID 101556Usaf DO-2Ausbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-phenyl-1-(2-phenyl[1,3]-dithian-2-yl)-ethanol (66) (2.50 g, 7.9 mmol) in 100 mL of a 9:1 mixture of acetonitrile and water was added mercuric perchlorate hydrate (4.1 g, 10.3 mmol). The resulting mixture was stirred at room temperature for 5 minutes and thin layer chromatography indicated that the reaction was completed. The mixture was diluted with ethyl acetate, filtered through a pad of Celite and the filtrate was washed with saturated NaHCO3, brine and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel, (20% ethyl acetate in hexanes) to afford 1.32 g (74%) of the title compound (67). 1H NMR (CDCl3, 400 MHz): δ 2.90 (dd, J=14.4, 7.0 Hz, 1H), 3.20 (dd, J=14.4, 4.0 Hz, 1H), 3.70 (d, J=6.8 Hz, 1H), 5.35 (m, 1H), 7.28-7.11 (m, 5H), 7.53 (m, 2H), 7.65 (m, 1H), 7.93 (d, J=7.2 Hz, 2H).

Aufarbeitung

  1. filtrationfiltered through a pad of Celite
  2. washthe filtrate was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by flash chromatography on silica gel, (20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c48e8de2886145c5a96e99166994f1eb
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238616B2

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