Propiolic Acid → cis-3-(Acetylthio)propenoic acid

HRID 374275Notes

Reaction equation

HRID 374275 reaction equation
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].[C:6]([OH:9])(=[S:8])[CH3:7]>C(O)C.C(N(CC)CC)C>[C:6]([S:8]/[CH:3]=[CH:2]\[C:1]([OH:5])=[O:4])(=[O:9])[CH3:7]

Participants

5

Reactant 2

HCID 10110Propiolic AcidHCID 178418634HCID 178418634, compound

Product 1

HCID 86746379cis-3-(Acetylthio)propenoic acidYield 117.9%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 702EthanolSolvent

Procedure

To a stirred, cooled (0° C.) solution of 1.0 ml (0.01625 mol) of propiolic acid in 12 ml of absolute ethanol under nitrogen was added 0.22 ml (0.0016 mol) of triethylamine. After 5 min, 1.45 ml (0.0203 mol) of thioacetic acid was added. After 20 h at 0° C. the reaction mixture was stripped of solvents to give 2.8 g of cis-3-(acetylthio)propenoic acid as a waxy solid. This product was used in the next step without further purification.

Workup

  1. waitAfter 20 h at 0° C. the reaction mixture was stripped of solvents

Sources & evidence

ORD record
ord-82b6ae811a3741fdb925161453dca0e6
Source dataset
uspto-grants-1992_11
Patent number
US05166390

Reaction notes

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