Water → 2,3-Diisopropoxy-4-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 21 (26.70 g, 158.7 mmol) in DMF (150 mL) under nitrogen, was added K2CO3 (65.84 g, 476.3 mmol) followed by 2-bromopropane (44.72 mL, 476.3 mmol) and heated to reflux (90° C.) for 12 hours. Water (200 mL) and EtOAc (200 mL) were added to the reaction mixture, the phases were separated, and the aqueous phase was extracted with EtOAc (3×200 mL). The combined organic solutions were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, elution with hexane) provided 32.85 g (1.30.2 mmol, 82%) of the diusopropyl-protected aldehyde 22 as a yellow oil.

Provenance & Evidence