Tetrahydrofuran → {[(2-Methylbut-3-yn-1-yl)oxy]methyl}benzene

A solution of BuLi (4.32 ml, 6.92 mmol) (1.6M in hexanes) was added dropwise to a stirred solution of the dibromo alkene (above, 1.1 g, 3.29 mmol) in dry THF (15 ml) under N2, such that the internal temperature <−70° C. The reaction was stirred at this temperature for 30 minutes and then quenched with saturated aqueous ammonium chloride (1 ml) before being allowed to warm to RT. The mixture was partitioned between diethyl ether and water. The aqueous layer was extracted with diethyl ether (×2). The combined extracts were washed with brine (×1), dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica, 1-4% Et2O/isohexane) to give the alkyne (0.55 g) as a colourless liquid.

1. customquenched with saturated aqueous ammonium chloride (1 ml)
2. customThe mixture was partitioned between diethyl ether and water
3. extractionThe aqueous layer was extracted with diethyl ether (×2)
4. washThe combined extracts were washed with brine (×1)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. customevaporated
8. customThe residue was purified by chromatography (silica, 1-4% Et2O/isohexane)

ORD 기록

ord-16b5265af9704caf8e914ab8a1d0cdb4

출처 데이터셋

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08389547B2