Reaktionsgleichung
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=1[C:9](O)=[O:10].B.C1COCC1.O>O1CCCC1>[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH:2]1[C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=1[CH2:9][OH:10]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To an ice cooled, stirred solution of the Compound 3b (5.00 g, 17.5 mmol) in tetrahydrofuran (100 mL) was added dropwise over 30 minutes 1.0 MBH3.THF (20 mL). The solution was allowed to warm to room temperature and was stirred overnight. Additional 1.0 M BH3.THF (5 mL) was added, and the solution was stirred another 4 hours. Water was added to hydrolyze the reaction, and the solution then was evaporated to dryness. The residue was dissolved in diethyl ether, and this solution was washed with a saturated solution of sodium carbonate, brine, and was dried over anhydrous magnesium sulfate. Evaporation of the solvent and recrystallization of the product from acetonitrile afforded the Compound 3c; m.p. 130°-131° C.; IR 3600 cm-1 (OH); 1H NMR (CDCl3 +D2O)δ1.8-2.2 (m, 2H, --CH2CH2CH2 --), 2.8-3.2 (m, 4H, --CH2CH2CH2 --), 4.61 (s, 2H, CH2O), 5.48 (s, 1H, SCHS), 7.7-8.3 (m, 3H, ArH).
Aufarbeitung
- additionwas added dropwise over 30 minutes 1.0 MBH3
- stirringthe solution was stirred another 4 hours
- customthe reaction
- customthe solution then was evaporated to dryness
- dissolutionThe residue was dissolved in diethyl ether
- washthis solution was washed with a saturated solution of sodium carbonate, brine
- dry with materialwas dried over anhydrous magnesium sulfate
- customEvaporation of the solvent and recrystallization of the product from acetonitrile
Quellen und Nachweise
- ORD-Eintrag
- ord-2160ea3d51d648ceac4d8cdc1cb0fcfb
- Quelldatensatz
- uspto-grants-1986_05
- Patentnummer
- US04590276
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