Iodine → HCID 59568794, compound

Temperature

63 °C

To a suspension of Mg turnings (134.0 mg, 5.6 mg-at.) and catalytic amount of iodine in 20 mL THF was added dropwise 2-(2-bromoethyl)-[1,3]dioxolane (500.0 mg, 2.8 mmol) with heating over a period of 30 min. After stirring the mixture for 30 min at 63° C. the reaction was cooled to −30° C. and 2-methyl-benzaldehyde (275.0 mg, 2.5 mmol) was slowly added as a solution in 5 mL THF. The temperature was maintained at −30° C. for 1 h and then slowly raised to room temperature over a period of 3 h. The excess Grignard reagent was destroyed by the careful addition of saturated aqueous NH4Cl (40 mL). The resulting mixture was extracted with ethyl acetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL). After evaporation of the solvent, the product was isolated by flash column chromatography eluting with 0 to 50% EtOAc/hexanes affording 290 mg of the title compound as a light yellow oil.

1. temperaturewith heating over a period of 30 min
2. temperaturewas cooled to −30° C.
3. temperatureThe temperature was maintained at −30° C. for 1 h
4. temperatureslowly raised to room temperature over a period of 3 h
5. customThe excess Grignard reagent was destroyed by the careful addition of saturated aqueous NH4Cl (40 mL)
6. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
7. washthe combined organic layers washed with brine (2×20 mL)
8. customAfter evaporation of the solvent
9. customthe product was isolated by flash column chromatography
10. washeluting with 0 to 50% EtOAc/hexanes affording 290 mg of the title compound as a light yellow oil

ORD record

ord-be1a19ae608048cf8b9f30c163e5dc3f

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119692B2