Triisopropyl borate → HCID 68783538, compound

Temperature

-78 °C

To a −78° C. stirred solution of the compound from step A (0.72 g, 2.18 mmol) in anhydrous toluene/THF (5 mL/3 mL) under nitrogen was added triisopropyl borate (0.53 g, 2.83 mmol) and then butyl lithium (2.5 M in hexanes, 1.22 mL, 3.05 mmol) slowly over about 10 min. After 10 min the dry ice bath was removed and stirring was continued for 20 min. The mixture was cooled at −78° C. and triisopropyl borate (0.32 g, 1.71 mmol) and butyl lithium (2.5 M in hexanes, 0.85 mL, 2.14 mmol) were added. The dry ice bath was removed and the mixture was allowed to warm to ambient temperature and was stirred for additional 20 min before quenching with a saturated solution of sodium bicarbonate (30 mL). The mixture was extracted with ethyl acetate (50 mL×2). The extracts were dried and contracted to give a solid. The solid was triturated with ethyl acetate/hexane (1:1) and dried to give the title compound (0.47 g, 81%).

1. customAfter 10 min the dry ice bath was removed
2. customThe dry ice bath was removed
3. temperatureto warm to ambient temperature
4. stirringwas stirred for additional 20 min
5. custombefore quenching with a saturated solution of sodium bicarbonate (30 mL)
6. extractionThe mixture was extracted with ethyl acetate (50 mL×2)
7. customThe extracts were dried
8. customto give a solid
9. customThe solid was triturated with ethyl acetate/hexane (1:1)
10. customdried

ORD record

ord-79c46ba2197b42f0849fd611c7ee6fa6

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07655662B2