[faust]

good morning,

I would like to make a TMS ketone (TMS-CO-R)

Is there an easiest way than : 1) R-CHO : protection with SH-CH2CH2-SH to make the diathiane. 2) BuLi / TMS 3) deprotection.

By the way, if you add a grignard reagent on a TMS ketone, do you make a Brook rearrangement?

Thanks

[KritikalMass]

Howdy,

I don't have any experience with this situation but maybe you could ask the moderator to move this post to the graduate student board- you may get quicker results over there.

[kiwi]

These are more usually called acyl silanes, they do undergo Brook rearrangements upon treatment with strong nucleophiles, and there seems to a couple of ways to make them. The thioacetal route looks popular, but addition of R3Si-Li to suitably derivatised carboxylic acids (acid chlorides, weinreb amides, morpholine amides) seems more direct. See for example http://www.orgsyn.org/orgsyn/prep.asp?prep=v84p0022. There is a reasonable writeup in Katritzky's Comprehensive Organic Functional Group Transformations book.