Hexane → 1-Chloro-2-(hept-1-en-6-yn-1-yl)benzene

Temperature

0 °C

An oven-dried 250 mL three-necked round-bottomed flask under a nitrogen atmosphere was charged with 3-chlorobenzylphosphonate (3.9 g, 15 mmol) and THF (60 mL). The solution was cooled to 0° C. in an ice bath for 15 min, then n-BuLi (12 mL of a 1.6 M n-hexane solution, 19 mmol) was added dropwise over 10 min via syringe. The mixture was stirred at 0° C. for 30 min, then aldehyde 4 (1.0 g, 10 mmol) in THF (40 mL) was added. The solution was warmed to rt and was stirred for 3 h. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 0.5:9.5). The reaction was quenched by adding sat'd aq ammonium chloride solution (70 mL). The layers were separated and the aqueous phase was extracted with ether (3×50 mL). The combined organic layers were washed with brine (2×50 mL), dried over Na2SO4, gravity filtered, and concentrated under reduced pressure. The reaction residue was purified by silica gel flash chromatography, eluting with AcOEt/n-hexane 0.5:9.5, to provide 1.11 g of the title compound as a colorless oil in a 54% yield.

1. temperatureThe solution was warmed to rt
2. stirringwas stirred for 3 h
3. customThe consumption of the starting material
4. customThe reaction was quenched
5. additionby adding sat'd aq ammonium chloride solution (70 mL)
6. customThe layers were separated
7. extractionthe aqueous phase was extracted with ether (3×50 mL)
8. washThe combined organic layers were washed with brine (2×50 mL)
9. dry with materialdried over Na2SO4, gravity
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe reaction residue was purified by silica gel flash chromatography
13. washeluting with AcOEt/n-hexane 0.5:9.5

ORD record

ord-b7d88a0d31f64c31899582e46786129b

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102703B2