Acetonitrile → 1-Trimethylsilanyloxy-4,5-dimethoxyindane-1-carbonitrile

HRID 1672439

Reaktionsgleichung

C[Si:2]([C:5]#N)([CH3:4])[CH3:3].[CH3:7][O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2=[O:20].[C:21](#[N:23])C>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+].[I-].[Zn+2].[I-]>[CH3:5][Si:2]([CH3:3])([CH3:4])[O:20][C:13]1([C:21]#[N:23])[C:14]2[C:10](=[C:9]([O:8][CH3:7])[C:17]([O:18][CH3:19])=[CH:16][CH:15]=2)[CH2:11][CH2:12]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Under nitrogen, zinc iodide (1.5 g, 4.68 mmol), trimethylsilyl cyanide (27.1 mL, 203.0 mmol) were added sequentially to the solution of 4,5-dimethoxy-1-indanone (30.0 g, 156.1 mmol) in toluene (100 mL) and acetonitrile (24 mL). The reaction mixture was heated to 50° C. for 16 h. The reaction mixture was cooled to room temperature and diluted with 100 mL of toluene and 60 mL of a saturated aqueous sodium bicarbonate solution. After the mixture was stirred for 1 h, the layers were separated. The organic layer was washed by brine (60 mL) and dried (Na2SO4). The organic layer was concentrated in vacuo and the residue was purified by chromatography (EtOAc/Hexanes: 5/95) to afford 1-trimethylsilanyloxy-4,5-dimethoxyindane-1-carbonitrile (33.1 g, 73%).

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
customthe layers were separated
washThe organic layer was washed by brine (60 mL)
dry with materialdried (Na2SO4)
concentrationThe organic layer was concentrated in vacuo
customthe residue was purified by chromatography (EtOAc/Hexanes: 5/95)

Quellen und Nachweise

ORD-Eintrag: ord-581e6cc5b894409ba8eb0381f926ec24
Quelldatensatz: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07998978B2

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