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| | Methyl 4-oxotetrahydrothiophene-3-carboxylate Basic information |
| | Methyl 4-oxotetrahydrothiophene-3-carboxylate Chemical Properties |
| Melting point | 37-38 °C | | Boiling point | 95 °C | | density | 1.309±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C(protect from light) | | solubility | Chloroform | | pka | 10.52±0.20(Predicted) | | form | Solid | | color | Light Yellow | | InChI | InChI=1S/C6H8O3S/c1-9-6(8)4-2-10-3-5(4)7/h4H,2-3H2,1H3 | | InChIKey | LEAKUJFYXNILRB-UHFFFAOYSA-N | | SMILES | C1SCC(=O)C1C(OC)=O | | EPA Substance Registry System | 3-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester (2689-68-1) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | TSCA | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29339900 |
| | Methyl 4-oxotetrahydrothiophene-3-carboxylate Usage And Synthesis |
| Chemical Properties | White solid | | Uses | Methyl 4-oxotetrahydrothiophene-3-carboxylate is used in the preparation of a new class of neuroleptic agents. | | Synthesis | 2,3,4,5-Tetrahydro-4-oxo-3-thiophene carboxylic acid, methyl ester (L75a): 25.3 g (1.1 mol) of sodium were implemented in 190 mL abs. methanol to methylate. To methylate solution 70 g (0.360 mol) (L74) was added dropwise at the boiling point and the reaction mixture was heated for 45 min under reflux. The cooling mixture was poured onto a mixture of 500 mL ice and 300 mL water, acidified with 100 mL conc. HCl and the oily precipitating product was brought to crystallize under cooling with ice/sodium chloride bath. The crystals were sucked off, resumed in 100 mL methylene chloride and dried over sodium sulfate and evaporated. There were obtained 16.7 g of pale beige crystals. The aqueous phase was extracted three times with 100 mL of methylene chloride, the organic phase dried over sodium sulfate and evaporated. 30 g of crystalline product Methyl 4-oxotetrahydrothiophene-3-carboxylate was obtained. Yield: 46.7 g of light beige crystals (81 % of theory). mp 29-31 degC. TLC: Bz:MeOH:AcOH = 45:8:4, Rf = 0.75.
 | | References | [1] Patent: US2016/204348, 2016, A1. Location in patent: Paragraph 0084; 0089
[2] Patent: WO2010/29577, 2010, A2. Location in patent: Page/Page column 41
[3] Patent: US2010/68178, 2010, A1. Location in patent: Page/Page column 17
[4] Patent: WO2006/102191, 2006, A1. Location in patent: Page/Page column 56; 87-88
[5] Journal of the American Chemical Society, 1946, vol. 68, p. 2229,2233 |
| | Methyl 4-oxotetrahydrothiophene-3-carboxylate Preparation Products And Raw materials |
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