Triethylsilane → ethyl (5-methyl-2,3-dihydro-1H-inden-2-yl)carbamate

HRID 1893514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893514
O[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[CH2:4][CH:3]1[NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16].C([SiH](CC)CC)C>ClCCCl.O>[CH3:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[CH2:4][CH:3]([NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])[CH2:2]2

Komponenten

5

Edukt 2

HCID 12052TriethylsilaneHCID 86650777ethyl (1-hydroxy-6-methyl-2,3-dihydro-1H-inden-2-yl)carbamate

Produkt 1

HCID 86650778ethyl (5-methyl-2,3-dihydro-1H-inden-2-yl)carbamateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

With stirring at room temperature, the compound (3.30 g, 13.9 mmol) obtained in step C, triethylsilane (4.4 ml, (27.8 mmol) and boron trifluoride-diethyl ether complex (3.4 ml, 27.8 mmol) dissolved in 1,2-dichloroethane (20 ml) were added to 1,2-dichloroethane (90 ml), and the mixture was stirred at 83° C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with water, and extracted with dichloromethane. The organic layer was washed with diluted aqueous sodium hydroxide solution, diluted hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to give the title compound (2.76 g, yield 91%) as a pale-yellow solid.

Aufarbeitung

  1. stirringthe mixture was stirred at 83° C. for 1 hr
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with diluted aqueous sodium hydroxide solution, diluted hydrochloric acid and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6c5553e576ea4c9e9597452e5754dd31
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513235B2

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