Silane, (4-methoxyphenyl)dimethyl- → (4-Methoxyphenyl)[3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilane

HRID 1639241Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]=[CH2:10])=[CH:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([SiH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=1>O1CCCC1.C(OCC)(=O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([Si:26]([CH2:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:4]=2)([CH3:27])[CH3:28])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a mixture of 1.14 g (0.005 mole) of 3-(4-fluoro-3-phenoxyphenyl)-1-propene and 0.004 g (0.00001 mole) of hydrogen hexachloroplatinate hydrate in 1 mL of tetrahydrofuran under nitrogen was added slowly 0.83 g (0.005 mole) of (4-methoxyphenyl)dimethylsilane. After completion of addition the reaction mixture was diluted with a mixture of petroleum ether and ethyl acetate. This solution was treated with activated carbon and then was filtered through a short column of silica gel. The solvent was evaporated under reduced pressure, leaving a residue. This residue was heated at 150° C. at 0.1 mm of Hg to remove impurities. The pot residue was a light brown liquid weighing 1.25 g. The ir and proton nmr spectra confirmed that this residue was (4-methoxyphenyl)[3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilane, compound 37 of Table 1.

Workup

additionAfter completion of addition the reaction mixture
additionThis solution was treated with activated carbon
filtrationwas filtered through a short column of silica gel
customThe solvent was evaporated under reduced pressure
customleaving a residue
customto remove impurities

Sources & evidence

ORD record: ord-18bcb1e40c404aa694f7e7155f92592e
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04883789

Reaction notes

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