Dimethylformamide → 2,3-Dihydrobenzofuran-6-carbaldehyde

Temperature

-78 °C

To a solution of 6-bromo-2,3-dihydro-1-benzofuran (190 mg, 0.955 mmol) in THF (4 ml) at −78° C. was added n-BuLi (1.313 ml, 2.100 mmol). The reaction mixture was stirred at −78° C. for 45 min then a solution of DMF (1.109 ml, 1.6 M in hexanes, 14.32 mmol) in THF (2 ml) was added dropwise and the reaction was stirred at −78° C. for 10 min then warmed to rt and stirred for 1 h. LCMS showed no starting material remaining. The reaction was stirred at rt for a further 2.5 h. The reaction mixture was poured cautiously into 2 M HCl (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with brine (50 ml), dried over MgSO4, filtered, evaporated and chromatographed (eluting 0-100% EtOAc/Hexane). The relevant fractions were combined and evaporated to deliver the product as a clear, colourless oil (44 mg, 0.297 mmol, 31%).

1. stirringthe reaction was stirred at −78° C. for 10 min
2. temperaturethen warmed to rt
3. stirringstirred for 1 h
4. stirringThe reaction was stirred at rt for a further 2.5 h
5. extractionextracted with ethyl acetate (3×50 ml)
6. washThe combined organic extracts were washed with brine (50 ml)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customevaporated
10. customchromatographed
11. wash(eluting 0-100% EtOAc/Hexane)
12. customevaporated

ORD record

ord-d6313059318f49a9955465ce3ddd5068

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389524B2