Ethanol → HCID 67166394, compound

Temperature

70 °C

At 5° C., o-tolyl-acetaldehyde (3.50 g, 29 mmol) is added to a mixture of POCl3 (7.5 mL, 93 mmol) and DMF (8 mL). The mixture is stirred at 70° C. for 3 h before the reaction is quenched by adding water/ice and NaOAc (17 g) and extracted with EA (2×150 mL). The solvent of the organic extract is evaporated and the product is purified by CC on silica gel eluting with heptane:EA 9:1. The resulting oil (2.5 g) is dissolved in ethanol (5 mL) and then added dropwise to a freshly prepared solution of Na (318 mg, 13.8 mmol) and ethyl-2-mercaptoacetate (1.64 g, 13.6 mmol) in ethanol (15 mL). The reaction mixture is stirred at rt for 16 h, then at 70° C. for 2 h. 3 M aq. NaOH (15 mL) is added and the mixture is stirred at 70° C. for 2 h. The mixture is cooled to rt, diluted with water and extracted with DCM. The aqueous phase is acidified with aq. HCl and extracted with EA. The organic extract is dried over MgSO4 and the solvent is evaporated to give crude 4-o-tolyl-thiophene-2-carboxylic acid (790 mg) as a brown solid; LC-MS: tR=0.91 min.

1. customis quenched
2. additionby adding water/ice and NaOAc (17 g)
3. extractionextracted with EA (2×150 mL)
4. extractionThe solvent of the organic extract
5. customis evaporated
6. customthe product is purified by CC on silica gel eluting with heptane:EA 9:1
7. dissolutionThe resulting oil (2.5 g) is dissolved in ethanol (5 mL)
8. stirringThe reaction mixture is stirred at rt for 16 h
9. waitat 70° C. for 2 h
10. stirringthe mixture is stirred at 70° C. for 2 h
11. temperatureThe mixture is cooled to rt
12. extractionextracted with DCM
13. extractionextracted with EA
14. extractionThe organic extract
15. dry with materialis dried over MgSO4
16. customthe solvent is evaporated

ORD record

ord-5c9093b836d14438ac8e0dec97580a7c

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07951794B2