Your deposition can either be done in the vapor phase or liquid phase. For vapor phase you can place your clean and dried sample in a desiccator with a small open vial of your silane overnight. The vapor pressure of the silane is high enough that it will fill the chamber with enough silane for a proper deposition. As for solution phase, you can use toluene as your medium. Depending on what you need (monolayer or a polymerized layer) the toluene should be dry or wet, respectively. The solution can be held at 70 deg C for about 10 - 30 minutes.
To determine whether the reaction occured, contact angle goniometry using water should have a value greater than 90 degrees.
Toluene will be able to solvate your ODS well. You could use ethanol if needed. A good catalyst will be an amine base, such as triethylamine. The triethylamine will deprotonate the silanol groups on the surface which will increase the reactivity of the surface.