Hydrochloric Acid → HCID 19434039, compound

Participants

Reaction Steps

A mixture of the product from Step C (5.86 g, 16.5 mmol) and trifluoroacetic acid (8 mL) in acetone (50 mL) was heated at reflux temperature for 1 h, cooled, and poured into water (100 mL). Acetone was evaporated and the aqueous was combined with a saturated aqueous solution of sodium bicarbonate (50 mL) and this mixture was extracted with ethyl acetate (2×150 mL). The combined extracts were dried (MgSO4) and evaporated to give a crude aldehyde which was dissolved in ethyl acetate (100 mL) followed by the addition of DBN (1 mL) and molecular sieves (5 g). This mixture was heated at reflux temperature for 15 min, cooled, and poured into 2N HCl (50 mL). The organic layer was separated, dried (MgSO4), and evaporated to dryness. Column chromatography (silica, 30% ethyl acetate/hexane) gave 3.60 g (79%) of an off-white solid: mp 87°-89° C.

Provenance & Evidence