Triisopropyl borate → HCID 22507227, compound

Temperature

0 °C

A −78° C. solution of 10.0 g (61.6 mmol) of 6-methoxy-5,6,7,8-tetrahydronaphthalene in 75 mL of THF was treated in a dropwise manner with 42.0 mL (67.2 mmol) of 1.6 M n-BuLi in hexanes. The mixture was stirred for 1 hr and was treated with 14.8 mL (64.1 mmol) of triisopropyl borate. The reaction was allowed to warm slowly to 0° C. and was stirred at this temperature for 0.5 hr. The reaction was quenched by the careful addition of 120 mL of aq 1N HCl. The layers were separated and the aqueous layer extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford a white solid which was used in part B without further purification.

1. stirringwas stirred at this temperature for 0.5 hr
2. customThe reaction was quenched by the careful addition of 120 mL of aq 1N HCl
3. customThe layers were separated
4. extractionthe aqueous layer extracted with EtOAc (3×50 mL)
5. dry with materialThe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto afford a white solid which
9. customwas used in part B without further purification

ORD record

ord-6058c86504b74f99b55aa5c392b08846

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06872743B2