Reaktionsgleichung
[OH:1][CH2:2][C:3]1[S:4][S:5][C:6]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:7][CH:8]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Si:11]([O:10][CH2:9][C:6]1[S:5][S:4][C:3]([CH2:2][O:1][C:20]2[CH:21]=[C:22]([C:25]([F:27])([F:28])[F:26])[CH:23]=[CH:24][C:19]=2[Cl:18])=[CH:8][CH:7]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred solution of 3-(hydroxymethyl)-6-[(tert-butyldimethylsilyloxy)methyl]-1,2-dithiin (U.S. Ser. No. 08/212,096) (200 mg, 0.688 mmol) in 5 mL dry THF was added a solution of 2-chloro-5-(trifluoromethyl) phenol (271 mg, 180 μL, 1.38 mmol) in 5 mL of THF, followed by the addition of triphenylphosphine (220 mg, 0.83 mmol). The resulting solution was cooled to 0° C., then 140 μL (155 mg, 0.89 mmol) of diethylazodicarboxylate was added, and the reaction mixture was kept at 0°-5° C. for 30 min and then the ice-water bath was removed. The reaction mixture was stirred at rt for 17 h. For isolation of the products the reaction mixture was chromatographed directly on a silica gel column, using ethyl acetate-hexane (1:3) as eluant, to yield 3-[(tert-butyldimethylsilyloxy)methyl]-6-[(2-chloro-5-trifluoromethyl-phenyloxy)methyl]-1,2-dithiin, 200 mg (62%); 1H NMR(CDCl3):δ7.54 (d, J=8, 1 H), 7.23 (d, J=8.4, 1 H), 7.16 (s, 1 H), 6.54 (d, J=6.4, 1 H), 6.42(d, J=6.4, 1 H), 4.78(s, 2 H), 4.31 (s, 2 H), 0.9 (s, 9 H), 0.1 (s, 6 H); MS (EI):m/z 468.1.
Aufarbeitung
- customthe ice-water bath was removed
- customFor isolation of the products the reaction mixture was chromatographed directly on a silica gel column
Quellen und Nachweise
- ORD-Eintrag
- ord-104bc34e8640485189a4dc2b0ea4bdce
- Quelldatensatz
- uspto-grants-1997_07
- Patentnummer
- US05648354
Verknüpfte Notizen
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