Diiodomethane → HCID 59779153, compound

Participants

Reaction Steps

To an Et2Zn solution (1.0M in hexane; 14 mL, 14 mmol) cooled to 0° C., a solution of CH2I2 (1.13 mL, 14 mmol) in CH2Cl2 (10 mL) was added. This was stirred for 5 min, then a solution of 3-(3,4-dichlorophenyl)cyclopent-2-en-1-ol (0.5 g, 2.19 mmol) in CH2Cl2 (50 mL) was added dropwise. The reaction mixture was stirred overnight then quenched with saturated aqueous NH4Cl. The reaction mixture was extracted with CH2Cl2 (3×). The combined organic phases were dried over MgSO4 and concentrated in vacuo. Purification of the crude material by silica gel chromatography using 10-30% EtOAc/Heptane as the eluting solvent gave the target compound (0.3 g, 64%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.76-0.85 (m, 1 H) 1.20-1.33 (m, 2 H) 1.65-1.77 (broad, 1 H) 1.83-1.90 (m, 1 H) 1.93-2.17 (m, 3 H) 4.64-4.73 (m, 1 H) 6.93-6.97 (m, 1 H) 7.22 (d, 1 H) 7.29-7.34 (m, 1 H).

Provenance & Evidence