Hydrochloric Acid → HCID 22723506, compound

Participants

Reaction Steps

4-Cyano-3-hydroxy-4-methylpentanoic acid (7.7 g, 49 mmol) was dissolved in DMF (50 mL) and potassium carbonate (10.16 g, 73.5 mmol) was added. Dimethyl sulfate (8.03 g, 63.7 mmol) was dropwise added with vigorous stirring. The mixture was stirred at room temperature for 2 hr and toluene (50 mL) was added. 2N Aqueous hydrochloric acid solution (40 mL, 80 mmol) was dropwise added with vigorous stirring. After partitioning, a toluene layer was separated and an aqueous layer was extracted again with toluene (25 mL). The toluene layers were combined and concentrated under reduced pressure to give methyl 4-cyano-3-hydroxy-4-methylpentanoate (7.13 g, 41.6 mmol). The yield was 85% relative to 4-cyano-3-hydroxy-4-methylpentanoic acid.

Provenance & Evidence