Reaktionsgleichung
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[SH:11].Br[CH2:13][CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1.O>C1COCC1>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11][CH2:13][CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1Komponenten
Versuchsvorschrift
Sodium hydride (60% dispersion in mineral oil) (120 mg, 3.01 mmol) was added to a solution of 2,4-difluorothiophenol (0.4 g, 2.74 mmol) in THF (10 mL) at 0° C., under argon. The reaction was allowed to warm to RT and 2-(3-bromopropoxy)tetrahydro-2H-pyran (672 mg, 3.01 mmol) added. The reaction was stirred at RT for 4 hours then poured into iced water (50 mL) and extracted into ethyl acetate (50 mL). The organics were washed with brine (50 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow oil which was chromatographed on silica, eluting with 0-10% ethyl acetate in isohexane, to give the desired compound as a colourless oil (610 mg). 1H NMR δ (CDCl3): 1.49-1.61 (m, 4H), 1.65-1.73 (m, 1H), 1.75-1.90 (m, 3H), 2.96 (t, 2H), 3.46-3.52 (m, 2H), 3.79-3.87 (m, 2H), 4.55-4.56 (m, 1H), 6.80-6.86 (m, 2H), 7.38-7.44 (m, 1H)
Aufarbeitung
- extractionextracted into ethyl acetate (50 mL)
- washThe organics were washed with brine (50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent removed in vacuo
- customto give a yellow oil which
- customwas chromatographed on silica
- washeluting with 0-10% ethyl acetate in isohexane
Quellen und Nachweise
- ORD-Eintrag
- ord-625c799b1a68490c8e253edfa9f45702
- Quelldatensatz
- uspto-grants-2011_05
- Patentnummer
- US07943607B2
Verknüpfte Notizen
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