Hydrochloric Acid → HCID 59026761, compound

Participants

Reaction Conditions

Reaction Steps

Isopropyl magnesium chloride (12.0 mL of a 2 M solution in THF, 24.0 mmol) was added to a solution of methyl 4-iodobenzoate (5.24 g, 20.0 mmol) in THF (50 mL) at −40° C. After 1 h, a second portion of isopropyl magnesium chloride (5.00 ml, of a 2 M solution in THF, 10.0 mmol) was added and the resulting mixture allowed to stir at −40° C. for 4 h. 3-Methyl-2-butanone (2.10 mL, 19.6 mmol) was then added and the resulting mixture allowed to warm to room temperature overnight. The reaction mixture was poured into 1 N HCl and extracted three times with EtOAc. The combined organic extracts were washed water, brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-20% EtOAc/hexanes as eluent) afforded the title compound i-2a. 1HNMR (500 MHz, CDCl3): δ 8.02 (d, 2H, J=8.5 Hz), 7.52 (d, 2H, J=8.5 Hz), 3.95 (s, 3H), 2.05 (p, 1H, J=6.6 Hz), 1.57 (s, 3H), 0.95 (d, 3H, J=6.6 Hz), 0.80 (d, 3H, J=6.9 Hz).

Provenance & Evidence