Potassium Carbonate → Tert-butyl(dimethyl)[(2-{[4-(trifluoromethoxy)phenoxy]methyl}-2-propenyl)oxy]silane

HRID 2066667Notes

Reaction equation

I[CH2:2][C:3](=[CH2:13])[CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[F:14][C:15]([F:25])([F:24])[O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:9]([Si:6]([CH3:8])([CH3:7])[O:5][CH2:4][C:3]([CH2:2][O:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:15]([F:14])([F:24])[F:25])=[CH:18][CH:19]=1)=[CH2:13])([CH3:12])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of iodide 165 (4.63 g, 14.8 mmol), 4-(trifluoromethoxy)phenol (3.10 mL, 23.9 mmol) and powdered K2CO3 (3.56 g, 25.8 mmol) in acetone (10 mL) was stirred at 50° C. for 11 h. The resulting cooled mixture was diluted with ice-water (100 mL) and extracted with CH2Cl2 (4×100 mL). The combined extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-3% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 5-10% CH2Cl2/petroleum ether gave tert-butyl(dimethyl)[(2-{[4-(trifluoromethoxy)phenoxy]methyl}-2-propenyl)oxy]silane (166) (3.12 g, 58%) as a colourless oil; 1H NMR (CDCl3) δ 7.12 (br d, J=9.0 Hz, 2H), 6.90 (dt, J=9.1, 2.9 Hz, 2H), 5.27 (d, J=0.7 Hz, 1H), 5.20 (d, J=1.1 Hz, 1H), 4.54 (s, 2H), 4.24 (s, 2H), 0.91 (s, 9H), 0.07 (s, 6H); HRFABMS calcd for C17H26F3O3Si m/z [M+H]+ 363.1603. found 363.1604.

Workup

temperatureThe resulting cooled mixture
extractionextracted with CH2Cl2 (4×100 mL)
customThe combined extracts were evaporated to dryness
customthe residue was chromatographed on silica gel
washElution with 0-3% CH2Cl2/petroleum ether firstly gave foreruns
washfurther elution with 5-10% CH2Cl2/petroleum ether

Sources & evidence

ORD record: ord-437284d6566449988b6d308e5a93464c
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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