Isopropenyl acetate → 286836-32-6

Temperature

100 °C

A mixture of 1.90 gm (10 mmol) 5-bromobenzofuran, 183 mg (0.6 mmol) tri(o-tolyl)phosphine, 4.3 mL (15 mMol) tributyl tin methoxide, and 1.7 mL (15.4 mMol) isopropenyl acetate in 55 mL toluene was sparged with nitrogen for 15 minutes. To this mixture were then added 54 mg (0.3 mMol) palladium(II) chloride and the mixture was heated to 100° C. for 3 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was filtered through a bed of 100 gm silica gel, eluting with 1 liter of 1:1 hexane:ethyl acetate. Fractions containing crude product were combined and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a gradient of hexane containing from 0–20% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide about 1.8 gm of the desired compound as an oil which gradually crystallized.

1. customwas sparged with nitrogen for 15 minutes
2. temperatureThe reaction mixture was cooled to room temperature
3. concentrationconcentrated under reduced pressure
4. filtrationThe residue was filtered through a bed of 100 gm silica gel
5. washeluting with 1 liter of 1:1 hexane
6. additionFractions containing crude product
7. concentrationconcentrated under reduced pressure
8. washeluting with a gradient of hexane containing from 0–20% ethyl acetate
9. additionFractions containing product
10. concentrationconcentrated under reduced pressure

ORD record

ord-fbc6a9d603e34bc796009c5a7363e8c4

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07045545B1