1,3-Propanedithiol → Methyl 2-(1,3-dithian-2-yl)acetate

Participants

Reaction Steps

Synthesis of both (1,3-dithian-2-yl)acetic acid 20 and (1,3-dithiolan-2-yl)acetic acid 19 is shown in Scheme 10. The syntheses start with commercially available (Aldrich) methyl 3,3-dimethoxypropionate 24. Cleavage of the dimethylacetal and reaction of the resulting aldehyde with ethane-1,2-dithiol or propane-1,3-dithiol would give methyl 2-(1,3-dithioian-2-yl)acetate and methyl 2-(1,3-dithian-2-yl)acetate, respectively. Hydrolysis of the esters would give 2-(1,3-dithiolan-2-yl)acetic acid 19 and 2-(1,3-dithian-2-yl)acetic acid 20. An alternative route to (1,3-dithiolan-2-yl)acetic acid has been reported (Jones & Kropp (1974) Synthetic Commun. 4:331-334).

Provenance & Evidence