Methyl iodide → HCID 19759894, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of diisopropylamine (4.44 mL, 31.7 mmol) in THF (200 mL) was cooled to -78° C. under an N2 atmosphere. A solution of n-butyllithium in hexane (12.3 mL, 2.58M) was added via syringe and the mixture stirred for 10 min at -78° C. and 15 min at 0° C. The mixture was cooled to -78° C. and product from Step B (5.3 g, 14.4 mmol) in THF (50 mL) was added dropwise. The reaction was stirred for 30 min and then methyl iodide (0.94 mL, 15.1 mmol) was added. The reaction was allowed to warm to room temperature overnight, and then quenched with water and 10% aqueous NaOH for 1 h. The DMF was removed in vacuo and water added. The aqueous solution was acidified with 6N HCl and extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over MgSO4. The solution was filtered and the filtrate freed of solvent to give the title compound (6.25 g, crude product). 1H NMR (300 MHz,DMSO-d6) 1.20(s,9H), 1.70(s,3H), 3.17(d,1H), 3.80(d,1H), 7.60(s,1H), 8.20(s,1H,exch.).

Provenance & Evidence