Tetrabutylammonium Fluoride → HCID 57825052, compound

HRID 1668766Notes

Reaction equation

C([Si]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([CH3:25])[CH:18]=2)=[CH2:16])[CH:10]=1)(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)=[CH2:16])=[CH:18][C:19]=1[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl-{3-[1-(4-methoxy-3-methyl-phenyl)-vinyl]-phenoxy}-dimethyl-silane (7.1 g, 19.8 mmol, 1.0 eq) was dissolved in 50 mL of dry tetrahydrofuran, the solution was cooled to 0° C. 21.8 mL of a tetrabutylammonium fluoride solution (1 M tetrahydrofuran, 21.8 mmol, 1.1 eq) was added and the mixture was allowed to warm up to room temperature. After 1 hour LCMS which showed complete conversion to the desired product. Water was added to the reaction mixture which was then extracted with ethyl acetate. The organic fraction was collected and dried with over sodium sulfate The crude product was purified by flash chromatography eluting with cyclohexane/ethylacetate (100:0 to 90:10). 5.3 g of clean product was obtained as colorless liquid (yield: 95%)

Workup

temperatureto warm up to room temperature

Sources & evidence

ORD record: ord-f331ad482bfa4b81b802e3e4394a1a19
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989449B2

Reaction notes

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