Ethanol → HCID 89649042, compound

1M DIBAL in toluene (7.53 mL, 7.53 mmol) was added dropwise over 10 mins to a stirred solution of methyl 4-(5-ethoxy-2-fluoro-phenyl)-6-methoxy-pyridine-2-carboxylate (which may be prepared as described in Description 131) (1.15 g, 3.77 mmol) in dry THF (20 mL) at −75° C. The reaction was stirred at this temp for 2 h then EtOH (175 μL) was added to quench. After 1 min the reaction mixture was poured into saturated Rochelle salt solution (100 ml) and water (50 ml). The mixture was warmed to ambient temperature then extracted with EtOAc (3×50 ml). Filtration under suction through celite was necessary to clear the emulsion. The combined organic extracts were dried (MgSO4) and evaporated to 4-(5-ethoxy-2-fluoro-phenyl)-6-methoxy-pyridine-2-carbaldehyde (D132) a slightly coloured oil (970 mg);

1. customto quench
2. additionAfter 1 min the reaction mixture was poured into saturated Rochelle salt solution (100 ml) and water (50 ml)
3. extractionthen extracted with EtOAc (3×50 ml)
4. filtrationFiltration under suction through celite
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. customevaporated to 4-(5-ethoxy-2-fluoro-phenyl)-6-methoxy-pyridine-2-carbaldehyde (D132) a slightly coloured oil (970 mg)

ORD record

ord-c82da6b3c3994403bbaaf2c9bb4d34c2

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376436B2