Iodine → 1,3-Dioxolane-2-propionaldehyde

Participants

Reaction Steps

To the solution of 2-(2-bromoethyl)-1,3-dioxolane (10 g, 55.2 mmol) in THF (50 mL) was added magnesium (1.6 g, 66.3 mmol) and trace amount of I2 as initiator. The reaction mixture was stirred at rt for 2 hrs. After cooling to −78° C., the mixture was quenched with dry DMF (1.39 g, 66.3 mmol) and kept at −78° C. for 2 hrs. After dilution with H2O the reaction mixture was extracted with CH2Cl2 (2×), followed by distillation (45-55° C.@8 mmHg) to afford 2 g (28%) of the title compound. MS (DCI/NH4+) m/z 131 (M+H)+.

Provenance & Evidence