Tetrahydrofuran → HCID 58213839, compound

To a solution of 1-(2-phenoxyethyl)-1H-pyrrole-2-carbaldehyde (0.68 g, 3.2 mmol) triethyl phosphonoacetate (0.76 mL, 3.8 mmol) in THF (20 mL) was added NaH (91 mg, 3.8 mmol. 60% wt.). The mixture was stirred for 2 hr at room temperature then diluted with ethyl acetate (100 mL) and washed with water (100 mL). The organic layer was dried (MgSO4), filtered and then concentrated. The crude ethyl ester was stirred in MeOH (20 mL) and NaOH (0.9 g, 22 mmol/dissolved in 10 mL H2O) was added. After stirring at room temperature for 24 hr, the solution was concentrated and then diluted with H2O (50 mL) and extracted with ether (2×100 mL). The aqueous layer was acidified (1N HCl) to pH=2-3 and then extracted with ethyl acetate (100 mL). The organic layer was dried (MgSO4), filtered and then concentrated to provide 0.47 g (58%) of (E)-3-(1-(2-phenoxyethyl)-1H-pyrrol-2-yl)acrylic acid as a light yellow solid.

1. washwashed with water (100 mL)
2. dry with materialThe organic layer was dried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated
5. stirringThe crude ethyl ester was stirred in MeOH (20 mL)
6. stirringAfter stirring at room temperature for 24 hr
7. concentrationthe solution was concentrated
8. additiondiluted with H2O (50 mL)
9. extractionextracted with ether (2×100 mL)
10. extractionextracted with ethyl acetate (100 mL)
11. dry with materialThe organic layer was dried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-399dca3b541e4a898cf3962cd7127fb6

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906954B2