Pentane → HCID 22731317, compound

A stirred, cooled (−78° C.) solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (Intermediate 2, 1.44 g, 6.2 mmol) in 18 mL of anhydrous ether and 5 mL of anhydrous tetrahydrofuran under argon, was treated with a 1.7M solution of t-butyllithium in n-pentane (7.65 mL, 13.02 mmol) and the resulting solution was stirred at the same temperature for 1 h. Trimethyl borate (1.6 mL, 13.02 mmol) was added and the reaction mixture was allowed warm from −78° C. to −30° C. over 2 h. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ether. The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to a foamy solid. Flash column chromatography using 25-100% ethyl acetate in hexane as the eluent afforded 0.57 g, 47.8% of the title compound as a white solid.

1. temperaturethe reaction mixture was allowed warm from −78° C. to −30° C. over 2 h
2. customThe reaction was quenched with saturated aqueous ammonium chloride solution
3. extractionextracted with ether
4. extractionThe combined organic extract
5. dry with materialwas dried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated to a foamy solid

ORD record

ord-6884b01c294144d69b60bfa4f7f2521e

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06720423B2