Dimethyl Sulfoxide → HCID 59835994, Verbindung

HRID 271994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271994
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([N:5]1[CH2:10][CH2:9][C:8]([CH2:17][CH2:18][OH:19])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:7][CH2:6]1)=[O:4].CS(C)=O.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([N:5]1[CH2:10][CH2:9][C:8]([CH2:17][CH:18]=[O:19])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:7][CH2:6]1)=[O:4]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 689336852-[3-(2,2-Dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethanol

Produkt 1

HCID 59835994HCID 59835994, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. solution of the above 2-[3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethanol, dimethyl sulfoxide (10 mL, 141 mmol) and diisopropylethylamine (10.5 mL, 60 mmol) in 60 mL CH2Cl2 was added SO3.pyr (9.0 g, 57 mmol) in one portion. The reaction mixture was stirred at 0° C. for 2 h, quenched with saturated aqueous NaHCO3, extracted with CHCl3, dried (Na2SO4) and chromatographed (2:1 Hex:EtOAc) to provide [3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]acetaldehyde (2.84 g, 98%) as an oil. 1H NMR (400 MHz, CDCl3): δ 9.64 (t, 1H, J=2.7 Hz), 7.45-7.41 (m, 4H), 7.33 (m, 1H), 5.49 (dd, 1H, J=11.1, 1.9 Hz), 4.74 (d, 1H, J=11.5 Hz), 4.27 (m, 1H), 3.08 (m, 1H), 2.72 (ABqd, 2H, J=15.3, 2.8 Hz), 2.43 (ddd, 1H, J=14.2, 4.1, 3.0 Hz), 2.11 (ddd, 1H, J=14.2; 11.4, 4.3 Hz), 1.28 (s, 9H). ESI-MS 312 (M+Na).

Aufarbeitung

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted with CHCl3
  3. dry with materialdried (Na2SO4)
  4. customchromatographed (2:1 Hex:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-aba813ce88c240f098975c565aa426d4
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452992B2

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