thionyl chloride

1.1: sodium hydroxide / methanol / 60 °C 1.2: pH 2 2.1: thionyl chloride / 3 h / 85 °C / |Inert atmosphere View Scheme

1.1: lithium diisopropyl amide; N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / |Inert atmosphere 1.2: 10 h / 20 °C / |Inert atmosphere 2.1: sodium hydroxide / methanol / 60 °C 2.2: pH 2 3.1: thionyl chloride / 3 h / 85 °C / |Inert atmosphere View Scheme

1: 1.) LDA / 1.) hexane, THF, 2.) reflux, 2 h 2: oxalyl chloride / 6 h / Ambient temperature View Scheme

1: aq. NaOH 2: SOCl2 View Scheme