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

HRID 1672439Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

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%).

Workup

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)

Sources & evidence

ORD record: ord-581e6cc5b894409ba8eb0381f926ec24
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998978B2

Reaction notes

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