Triethylamine → Acetophenone

Into a 500 mL single-neck flask fitted with a stirrer and thermometer, 10.0 g. of 4′-iodoacetophenone, 1.0 g. of PdCl2(dppf), and 17 mL triethylamine were placed in Dioxane (160 mL) and stirred at room temperature under a nitrogen atmosphere. This solution was then degassed with nitrogen for 15 minutes, followed by the addition of 8.8 mL pinacol borane syringe wise. Addition was exothermic and the solution turned dark immediately. The reaction was then heated at 85° C. for 6 h. The mixture was then cooled to room temperature and poured into H2O and the desired product was extracted with ether. This organic layer was washed with H2O, dried over MgSO4, and concentrated under reduced vacuum to yield a white solid. This material was purified via silica gel chromatography employing the Water's prep. 2000 and eluting with hexane/ethyl acetate 19:1 to yield intermediate title compound, acetophenone derivative, (6.4 g, 64%) as a white powder.

1. customInto a 500 mL single-neck flask fitted with a stirrer
2. customThis solution was then degassed with nitrogen for 15 minutes
3. additionfollowed by the addition of 8.8 mL pinacol borane syringe wise
4. additionAddition
5. temperatureThe reaction was then heated at 85° C. for 6 h
6. temperatureThe mixture was then cooled to room temperature
7. additionpoured into H2O
8. extractionthe desired product was extracted with ether
9. washThis organic layer was washed with H2O
10. dry with materialdried over MgSO4
11. concentrationconcentrated under reduced vacuum
12. customto yield a white solid
13. customThis material was purified via silica gel chromatography
14. wash2000 and eluting with hexane/ethyl acetate 19:1

ORD record

ord-8558ea726b6144be9789dd0d461383b6

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07034045B1