Tetrahydrofuran → HCID 19081868, compound

Participants

Reaction Conditions

Reaction Steps

4-Amino-5-chloro-2-methoxyacetophenone (12.75 g, 64 mmol), prepared as in Example 5, was suspended in THF (125 mL). The suspension was added to a -50° C. solution of lithium diisopropylamide (16.1 g, 150 mmol) in THF (200 mL) and the mixture was stirred at 0° C. for 15 minutes. Pyridine-4-carboxaldehyde (8.0 g, 75 mmol) was added and the mixture was allowed to warm to 5° C. Aqueous ammonium chloride was added and the mixture was extracted three times with ethyl acetate. The combined extracts were washed with water, dried over sodium sulfate, and concentrated in vacuo to leave a semi-solid residue. Ethyl acetate-hexane was added and filtration gave 1-(4-amino-5-chloro-2-methoxyphenyl)-3-hydroxy-3-(pyridin-4-yl)propan-1-one (12.1 g, 40 mmol), m.p. 181°-183° C.

Provenance & Evidence