Ethanol → 4-(5-Ethoxy-2-fluoro-phenyl)-5,6-dimethyl-pyridine-2-carbaldehyde

1M DIBAL in toluene (8.7 mL, 8.7 mmol) was added dropwise over 12 minutes to a stirred solution of methyl 4-(5-ethoxy-2-fluoro-phenyl)-5,6-dimethyl-pyridine-2-carboxylate (which may be prepared as described in Description 52) (1.32 g, 4.35 mmol) in dry THF (25 mL) at −75° C. The reaction was stirred at this temp for 2.5 h then EtOH (0.2 ml) was added to quench. After 1 minute the reaction was poured into saturated Rochelle salt solution (200 ml). The mixture was extracted with EtOAc (100 ml) then DCM (2×100 ml). The combined organic extracts were dried (Na2SO4), filtered and evaporated to a white solid, which was dried at RT under vacuum for 16 h to afford 4-(5-ethoxy-2-fluoro-phenyl)-5,6-dimethyl-pyridine-2-carbaldehyde (D53) (1.17 g);

1. customto quench
2. additionAfter 1 minute the reaction was poured into saturated Rochelle salt solution (200 ml)
3. extractionThe mixture was extracted with EtOAc (100 ml)
4. dry with materialThe combined organic extracts were dried (Na2SO4)
5. filtrationfiltered
6. customevaporated to a white solid, which
7. customwas dried at RT under vacuum for 16 h

ORD record

ord-7b60212f49d14da99d5b0ab6e175f865

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376436B2