Diethyl Ether → HCID 68955002, Verbindung

HRID 132617

Reaktionsgleichung

Reaktionsgleichung von HRID 132617
CCOCC.[CH2:6]([Mg]Cl)[CH2:7][CH3:8].[C:11]([N:16]1[C@H:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][O:18][C:17]1=[O:27])(=[O:15])[CH:12]=[CH:13][CH3:14]>C1COCC1>[CH3:14][C@H:13]([CH2:6][CH2:7][CH3:8])[CH2:12][C:11]([N:16]1[C@H:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:19][O:18][C:17]1=[O:27])=[O:15]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 53753523HCID 53753523, VerbindungHCID 178455855HCID 178455855, Verbindung

Produkt 1

HCID 68955002HCID 68955002, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To the copper (1) bromide dimethylsulfide complex (13.34 g, 64.87 mmol) in dry THF (150 mL) at −30° C. under Nitrogen was added a 2M ether solution of Propylmagnesiumchloride (64.87 mL, 129.7 mmol) and stirred for 20 minutes. (R)-3-But-2-enoyl-4-phenyl-oxazolidin-2-one (15.0 g, 64.87 mmol) in THF (60 mL) was added over a 15 minute period at −35° C. and let slowly warm up to room temperature over 4 hours. The mixture was cooled to 0° C. and quenched with saturated ammonium chloride solution. The suspension was extracted into ether, washed with 5% ammonium hydroxide solution and then with brine and dried over MgSO4. The solution was concentrated under reduced pressure to afford the titled compound (13.34 g; 100% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 0.8 (m, 6H) 1.2 (m, 3H) 1.6 (s, 1H) 2.0 (m, 1H) 2.7 (dd, J=16.1, 8.5 Hz, 1H) 3.0 (dd, J=15.9, 5.4 Hz, 1H) 4.3 (dd, J=8.9, 3.8 Hz, 1H) 4.7 (t, J=8.9 Hz, 1H) 5.4 (dd, J=8.8, 3.9 Hz, 1H) 5.4 (dd, J=8.8, 3.9 Hz, 1H) 7.3 (m, 5H). MS, m/z (relative intensity): 276 [M+1H, 100%].

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with saturated ammonium chloride solution
  3. extractionThe suspension was extracted into ether
  4. washwashed with 5% ammonium hydroxide solution
  5. dry with materialwith brine and dried over MgSO4
  6. concentrationThe solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7568c0302bcd4358b551785dcca9458f
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388023B2

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