3-HYDROXY-2-METHYL-CYCLOPENT-2-ENONE synthesis

Yield:-

Steps:

Multi-step reaction with 5 steps
1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; methyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
1.3: 3 h / -78 - 20 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / benzene / 6 h / Reflux; Dean-Stark
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / Inert atmosphere
3.2: 20 h
4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
5.1: hydrogenchloride / tetrahydrofuran; water / 10 h

References:

Yu, Guojun;Clive, Derrick L. J. [Organic and Biomolecular Chemistry,2016,vol. 14,# 5,p. 1653 - 1664]