Methyl Acrylate → HCID 21867438, Verbindung

To a solution of the ester from Step 3 (0.5 g, 1.76 mmol) in toluene (7 mL) and THF (1 mL) at RT was added 1M potassium t-butoxide (1.76 mL, 1.76 mmol). After 15 minutes, methyl acrylate (0.32 mL, 3.5 mmol) was added, and the mixture was brought to reflux for 1.5 hours. The reaction was quenched by the addition of saturated NH4Cl solution, and the product was extracted with EtOAc/THF. The organic layer was washed with H2O and brine, dried (MgSO4), filtered, and evaporated. The intermediate was suspended in EtOH (10 mL), and concentrated HCl (2 mL) was added. After heating to reflux for 2 hours, the mixture was cooled and diluted with H2O (30 mL). The product was extracted with CH2Cl2 and the organic phase was washed with H2O before drying (MgSO4). Following filtration and removal of solvent under vacuum, the product was stirred with 1:2 EtOAc:hexane to give a tan-coloured solid (0.4 g).

1. temperatureto reflux for 1.5 hours
2. customThe reaction was quenched by the addition of saturated NH4Cl solution
3. extractionthe product was extracted with EtOAc/THF
4. washThe organic layer was washed with H2O and brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. additionconcentrated HCl (2 mL) was added
9. temperatureAfter heating
10. temperatureto reflux for 2 hours
11. temperaturethe mixture was cooled
12. additiondiluted with H2O (30 mL)
13. extractionThe product was extracted with CH2Cl2
14. washthe organic phase was washed with H2O
15. dry with materialbefore drying (MgSO4)
16. filtrationfiltration and removal of solvent under vacuum

ORD-Eintrag

ord-6e605b4f914b4fa9a8cf25d29470fb32

Quelldatensatz

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07144913B2