1,1-Diethyl cyclopent-3-ene-1,1-dicarboxylate → [1-(Hydroxymethyl)cyclopent-3-en-1-yl]methanol

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled suspension of lithium aluminum hydride (25.54 g, 672.8 mmol) in tetrahydrofuran (2 L) was added a solution of diethyl cyclopent-3-ene-1,1-dicarboxylate (42.0 g, 198 mmol) in tetrahydrofuran (100 mL) over 30 min. The reaction mixture was warmed to 26° C. After 2 h, the reaction was diluted sequentially with water (26 mL), 3M aqueous sodium hydroxide solution (26 mL), and water (78 mL). The mixture was stirred at 0° C. for 15 min and filtered. The filtrate was concentrated to afford product as a colorless oil (45 g, 89% yield).

Provenance & Evidence