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

HRID 1261376Notes

Reaction equation

HRID 1261376 reaction equation
[S:1]1[CH2:6][CH2:5]C[S:3][CH:2]1[CH2:7][C:8]([OH:10])=[O:9].S1CCS[CH:12]1CC(O)=O.[CH3:20][O:21][CH:22]([O:28]C)[CH2:23][C:24](OC)=O.C(S)CS.[CH2:34]([SH:38])[CH2:35][CH2:36][SH:37]>>[S:3]1[CH2:5][CH2:6][S:1][CH:2]1[CH2:7][C:8]([O:10][CH3:12])=[O:9].[S:37]1[CH2:36][CH2:35][CH2:34][S:38][CH:24]1[CH2:23][C:22]([O:21][CH3:20])=[O:28]

Participants

7

Reactant 5

HCID 80131,3-PropanedithiolHCID 109021,2-EthanedithiolHCID 81924Methyl 3,3-dimethoxypropionateHCID 12402571(1,3-Dithian-2-yl)acetic acidHCID 15013246(1,3-Dithiolan-2-yl)acetic acid

Product 2

HCID 10535770Methyl 2-(1,3-dithian-2-yl)acetateHCID 13302458Methyl 2-(1,3-dithioian-2-yl)acetate

Procedure

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).

Sources & evidence

ORD record
ord-6ce7e77ef9fc4b80b8076703a0488dcb
Source dataset
uspto-grants-2013_06
Patent number
US08470861B2

Reaction notes

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