Diethyl Ether → HCID 178458286, compound

To a solution of triphenylphosphine methyl bromide (0.486 mmol) in diethyl ether (15 mL) at room temperature was added nBuLi (0.486 mmol, 2.5 M) and the suspension was stirred for 2.5 h. 1-(benzofuran-3-yl)-2-(2-(1-trityl-1H-imidazol-4-yl)phenoxy)ethanone (0.442 mmol) was added as a solution in diethyl ether (2 mL) at room temperature. After stirring overnight the reaction mixture was diluted with water (10 mL) and the product was extracted with EtOAC (3×30 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to afford the crude product. The crude was stirred in a mixture of acetic acid (1.5 mL) and MeOH at 80° C. for 2 h. After cooling to room temperature the mixture was stripped off the solvents and the crude was diluted with satd. Na2CO3 solution and the product was extracted with EtOAc (3×30 mL). The combined organic extract was dried over Na2SO4 and concentrated to afford the crude. Chromatographic purification afforded the final product. Yield 44%. 1H NMR: 5.01 (s, 2H), 5.63 (s, 1H), 5.89 (s, 1H), 7.06 (d, 1H, J=6.69 Hz), 7.08 (d, 1H, J=5.10 Hz), 7.23-7.44 (m, 5H), 7.54 (d, 1H, J=7.59 Hz), 7.74 (s, 1H), 7.81 (s, 1H), 7.84 (s, 1H)

1. stirringAfter stirring overnight the reaction mixture
2. extractionthe product was extracted with EtOAC (3×30 mL)
3. dry with materialThe combined organic extracts were dried (Na2SO4)
4. concentrationconcentrated under reduced pressure
5. customto afford the crude product
6. additionthe crude was diluted with satd
7. extractionNa2CO3 solution and the product was extracted with EtOAc (3×30 mL)
8. extractionThe combined organic extract
9. dry with materialwas dried over Na2SO4
10. concentrationconcentrated
11. customto afford the crude
12. customChromatographic purification

ORD record

ord-a5287570556b4ae9a96f13746cc418cd

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722720B2