Methyl iodide → HCID 67996655, compound

Participants

Reaction Conditions

Reaction Steps

To the intermediate from Step A (1.35 g, 8.71 mmol) and HMPA (6.24 g, 34.8 mmol) in 10 mL of THF at −78° C. was added dropwise a LDA solution (2.0 M, 5.22 mL, 10.5 mmol). The mixture was stirred at −78° C. for 30 min and MeI (1.48 g, 10.45 mmol) was added dropwise. The resulting mixture was slowly warmed to room temperature. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The organic phase was washed with brine, dried with MgSO4, and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated compound (yellow oil). 1H NMR (CDCl3, 500 MHz) δ 7.48 (1H, s), 3.77 (3H, s), 3.76 (1H, q, J=7.5 Hz), 2.49 (3H, s), 1.55 (3H, d, J=7.5 Hz).

Provenance & Evidence