# Conversion of an alcohol to a methyl group

I'm only interested in the first conversion: D to E.

I've been thinking about this for a little bit. My first thought was to use $\ce{TsCl}$ to make a good leaving group then a $\ce{Me}$ nucleophile. This didn't seem like it would work since $\ce{Li-Me/MeMgBr}$ would just displace the leaving group. My second thought was to convert the alcohol to a halide, make it a Grignard reagent, then react it with $\ce{MeBr}$. But that also wouldn't work. Any suggestions?

• Consider going via ketone. – permeakra May 15 '18 at 21:25
• You might also consider an organocuprate as a nucleophile. Ordinarily, I wouldn't suggest a secondary electrophile for SN2, but this is also benzylic so... – Zhe May 15 '18 at 21:30
• I considered ketone, that would add the methyl easily using Me-Li then an OH would be left. Add TsCl then a weak reducing agent, NaB(CN)H3, but would that work to remove the OH? – Malcolm Hall May 15 '18 at 21:48
• Oxidise to ketone, Wittig, then hydrogenate – orthocresol May 15 '18 at 23:38
• @MalcolmHall It should, but there is a more reliable way. The resulting alcohol should dehydrate really easy. In fact, it might dehydrate during acidic treatment of Grignard reagent adduct. – permeakra May 16 '18 at 4:15

1. add $\ce{HBr}$