4-Iodotoluene → HCID 11008393, compound

Temperature

-20 °C

A solution of 4-iodotoluene (10 g, 45 mmol) in THF (300 mL) at −78° C. was treated with a solution of n-butyllithium (2.5 M in hexanes; 20 mL, 50 mmol) such that the reaction temperature remained ≦−78° C. After 15 minutes, a solution of 3-methoxy-2-cyclopenten-1-one (5.78 g, 52 mmol) in THF (50 mL) was added such that the reaction temperature remained ≦−78° C. The reaction mixture was warmed to −20° C. over 2 h, quenched with a solution of 1N HCl and concentrated in vacuo to remove THF. A solution of 1N HCl (40 mL) was added, the solution was stirred for 30 min and extracted with EtOAc (3×). The combined organic extracts were washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography using heptane/EtOAc as the eluting solvent to afford 4.92 g of 3-p-tolyl-cyclopent-2-enone as a white powder (Yield 63.5%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.42 (s, 3 H) 2.59 (ddd, J=4.83, 2.64, 2.49 Hz, 2 H) 3.05 (td, J=4.98, 1.76 Hz, 2 H) 6.55 (t, J=1.66 Hz, 1 H) 7.27 (d, J=8.00 Hz, 2 H) 7.57 (dt, J=8.30, 1.90 Hz, 2 H).

1. customremained ≦−78° C
2. customremained ≦−78° C
3. customquenched with a solution of 1N HCl
4. concentrationconcentrated in vacuo
5. customto remove THF
6. additionA solution of 1N HCl (40 mL) was added
7. extractionextracted with EtOAc (3×)
8. washThe combined organic extracts were washed with saturated aqueous NaHCO3, brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified by silica gel chromatography

ORD record

ord-d48eee1f045546cba0f83fcc4091dc7f

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138377B2