Methanol → HCID 123884592, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 mL three-necked RBF were added 2-(2,6-dichloro-3-fluorophenyl)-2-((trimethylsilyl)oxy)acetonitrile (0.50 g, 1.711 mmol) and DCM (9 ml). The reaction mixture was purged with nitrogen and cooled to −64° C. Under a nitrogen atmosphere, diisobutylaluminum hydride, 1.0 M solution in hexane (2.6 ml, 2.6 mmol) was added dropwise. The mixture was stirred at −64° C. After 2 h, the reaction was quenched. While maintaining temp <−65° C., MeOH (1.4 ml, 34.2 mmol) was carefully added dropwise to the reaction mixture followed by saturated Rochelle salt solution (5 mL). The mixture was allowed to reach room temperature and stirred for 30 min. Water and DCM were added and the aqueous layer was extracted with DCM. The combined organic layer washed with brine, dried over anhydrous MgSO4, and concentrated to afford 2-(2,6-dichloro-3-fluorophenyl)-2-((trimethylsilyl)oxy)acetaldehyde as a colorless oil (0.517 g, crude).

Provenance & Evidence