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(sorry about the poor diagram. I don't know how to add in the arrows and stuff)

Draw the product when the following compound is reacted with sisyl chloride in the presense of DMF catalyst at $\pu{-10^\circ C}$?

My Attempt

I know that sisyl methyl is a silicon protecting group that readily forms $\ce{Si-O}$ bonds. However I am not entirely sure how the different steric environments will effect which oxygen is protected.

I am guessing that the primary alcohol group will get protected since it is a primary alcohol, hence there will be less steric hindrance for the bulky sisyl chloride molecule to attack the primary alcohol group compared to the secondary alcohol group.

I am not sure if there are other factors that effect which oxygen will get protected. For example, I am not sure the effect of the double bond on the secondary alcohol (I don't think that there is an effect since it is too far away).


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