Reaction #163435

Reaction equation

DMF

2-(2-bromoethyl)-1,3-dioxolane

magnesium

I2

→

title compound

Yield 28.0%

3-(1,3-dioxolan-2-yl)propanal

Yield 28.0%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureAfter cooling to −78° C.
2. 2
   workup.WAITkept at −78° C. for 2 hrs
3. 3
   ExtractionAfter dilution with H2O the reaction mixture was extracted with CH2Cl2 (2×)
4. 4
   workup.DISTILLATIONfollowed by distillation (45-55° C. @ 8 mmHg)

Procedure

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)+.

Source