Diethyl Ether → HCID 15728747, Verbindung

To 3-thiophenecarboxaldehyde dimethyl acetal (11.9 g) and ether (180 ml) was added n-butyllithium (31.0 ml, 2.5M in hexanes) at a rate so as to maintain gentle reflux of the solvent. The mixture was heated under reflux for 0.5 hr, cooled to ambient temperature, diluted with tetrahydrofuran (50 ml), was cooled to -78° C., and 2-fluorobenzaldehyde (8.50 ml) in tetrahydrofuran (90 ml) was added. The reaction mixture was allowed to warm to ambient temperature over several hrs and was quenched with dilute aqueous ammonium chloride solution and ether. The layers were separated and the organic layer was washed with dilute aqueous ammonium chloride solution. The combined aqueous layers were back-extracted with ether, and the combined organic layers were washed with brine, dried over anhydrous potassium carbonate, and filtered. Concentration of the residue afforded 3-(dimethoxymethyl)-α-(2-fluorophenyl)-2-thiophenemethanol.

1. temperatureto maintain gentle
2. temperaturereflux of the solvent
3. temperatureThe mixture was heated
4. temperatureunder reflux for 0.5 hr
5. temperaturewas cooled to -78° C.
6. temperatureto warm to ambient temperature over several hrs
7. customwas quenched with dilute aqueous ammonium chloride solution and ether
8. customThe layers were separated
9. washthe organic layer was washed with dilute aqueous ammonium chloride solution
10. extractionThe combined aqueous layers were back-extracted with ether
11. washthe combined organic layers were washed with brine
12. dry with materialdried over anhydrous potassium carbonate
13. filtrationfiltered

ORD-Eintrag

ord-da9fac082ae34f63ab686b979bfbe504

Quelldatensatz

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05260319