Hydrogen Peroxide → 5-propyl-6,7-dihydro-1-benzothiophen-4(5H)-one
Reaktionsgleichung
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[O:10])[C:4]=2[CH:3]=[CH:2]1.C(B(CC)CC)C.I[CH2:19][CH2:20][CH3:21].[OH-].[Na+].OO>O1CCCC1>[CH2:19]([CH:8]1[C:9](=[O:10])[C:4]2[CH:3]=[CH:2][S:1][C:5]=2[CH2:6][CH2:7]1)[CH2:20][CH3:21]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of KH (30%, 11.44 g) in tetrahydrofuran (160 ml) under N2 was added dropwise 6,7-dihydro-1-benzothiophen-4(5H)-one (8 g) in tetrahydrofuran (40 ml). After 30 min, a triethyl borane (97 ml, 1 M THF) solution was added dropwise over 5 min. After 10 min, iodopropane was and the reaction stirred for 16 h. The reaction mixture was cooled to 0° C. and 1 N NaOH (250 ml) and hydrogen peroxide (12 ml, 30%) was added. The reaction mixture stirred for 1 h and was extracted with 400 ml ethyl acetate. The organic layer was washed with saturated sodium thiosulfate, dried MgSO4, filtered and concentrated. MPLC chromatography on a biotage 40 L with 4% ethyl acetate/heptane provided the title compound as an oil (8.21 g, 80%): 1H NMR (300 MHz, CDCl3) δ) 7.40, 7.07, 3.15-3.01, 2.47, 2.32, 2.07-1.88, 1.53-1.30, 1.27, 0.99-0.88; HRMS (FAB) calcd for C11H14OS+H 195.0844, found 195.0835.
Aufarbeitung
- waitAfter 10 min
- stirringThe reaction mixture stirred for 1 h
- extractionwas extracted with 400 ml ethyl acetate
- washThe organic layer was washed with saturated sodium thiosulfate, dried MgSO4
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-525ae72c613f43ab87f0b367dd87f09b
- Quelldatensatz
- uspto-grants-2006_01
- Patentnummer
- US06992087B2
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