# What will methyl (2-oxocyclohexyl)acetate produce when reacted with sodium borohydride?

What will methyl (2-oxocyclohexyl)acetate produce when reacted with sodium borohydride?

I feel the answer should be 2-(2-hydroxypropyl)cyclohexan-1-one:

Because the carbonyl carbon on the aliphatic chain should be more electrophilic than the one on the ring due to the presence of two neighbouring electronegative oxygen atoms. Correct me if I am wrong but I think the reaction begins with the hydride ion which acts as a nucleophile?

On the other hand the answer given in my book is 1-(2-hydroxycyclohexyl)propan-2-one:

• FYI: The Luche reduction uses a lanthanide chloride to coordinate a carbonyl oxygen accompanied by $\alpha, \beta$ unsatur-ation (hyphenated because device autocorrect is getting weird), activating that carbonyl group for the borohydride attack. Mar 9 '18 at 13:42