Methane → [4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]acetic acid

Participants

Reaction Steps

To a solution of ethyl[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]acetate (Preparation 293, 36.4 g, 151 mmol) in water (50 mL), was added a solution of NaOH (7.60 g, 190 mmol) in water (25 mL). The solution was refluxed with activated charcoal, filtered through Celite, and NaHSO4 (25.8 g, 190 mmol) added. EtOAc (50 mL) was added to the filtrate. The formed precipitate was separated by filtration, dissolved in EtOAc (100 mL), and the solution was filtered. The water layer was extracted with EtOAc (10×50 mL), and the combined extracts were evaporated to a volume of 100 mL. The precipitate was filtered, washed with ethyl acetate (2×50 mL), and concentrated under reduced pressure to afford the title compound as a colorless crystalline substance in 87% yield, 27.8 g. mp 124.0-126.0° C.; MS m/z 212 [M+H]+

Provenance & Evidence