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enter image description hereWhat protecting group can I use that will protect the thiol in the presence of an alcohol? Is there a set of conditions, or a group that I can use that is selective to the thiol over the alcohol?

I am converting an acid halide into an ester whose R group's terminal is a thiol. I will be using 3-Mercapto-1-propanol. I want to make sure that the acid only reacts with the alcohol side, so I can use the thiol group in the next step.

EDIT: I added the general reaction scheme for reference

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    $\begingroup$ How about oxidising it to the disulfide then running the (di)ester formation then reducing back to the thiol? The disulfide is commercially available alfa-chemistry.com/cas_177854-95-4.htm $\endgroup$
    – Waylander
    Commented Apr 25, 2023 at 17:33
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    $\begingroup$ 2-Hydroxyethyldisulfide is commercially available. You can use it as substrate for esterification and then reduce the resulting ester to thiols as Waylander suggested. $\endgroup$
    – Mathew Mahindaratne
    Commented Apr 25, 2023 at 18:57

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