Beta-Propiolactone → 1-(2-Hydroxyethyl)cyclopentan-1-ol

Participants

Reaction Steps

1,4-dibromobutane (10 g, 46.3 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg) as initiator. The mixture was stirred at rt for 3 h. To the mixture was added dropwise oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL). The reaction was stirred at rt for 12 h, quenched with saturated NH4Cl, and the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The organic layers were combined and dried over MgSO4, filtered and concentrated. The residue was purified by distillation at 95-100° [email protected] Torr to provide the title compound (1.1 g, 18%). MS (DCI/NH3) m/z 148 (M+NH4)+.

Provenance & Evidence