Toluene → 4,4,6-Trimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Participants

Reaction Steps

To a solution of Compound 14A (11.8 mmol, 1.95 g) in 200 mL THF was added Et3N (29.6 mmol, 4.06 mL) at 0° C. followed by a dropwise addition of a solution of phosgene in toluene (20% solution, 12.19 mmol, 7.9 mL). The reaction mixture was stirred at r.t. overnight It was extracted with Et2O, washed with water and brine. The organic layer was dried over Na2SO4, filtered and the solvent was removed in vacuo to the desired product (2.14 g, expected wt.=2.25 g) which was used in the next step without further purification. MS (electrospray): mass calculated for C11H13NO2, 191.09, m/z found 192 (100%), [M+H]+.

Provenance & Evidence