Carbon Tetrachloride → dibenzyl 3-(2,3-dihydro-1H-inden-5-yl)-6-isopropyl-2-oxo-4-thioxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-7-yl phosphate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 0.30 g (0.84 mmols) of 5 in 10 mL of anhydrous acetonitrile at 5° C., was added 0.4 mL (4.24 mmols) of CCl4, 0.31 mL (1.78 mmols) of diisopropylethylamine and 10 mg (85□mols) of 4-dimethylaminopyridine in that order. After stirring the mixture for 5 min. at 5° C., 0.34 mL (1.27 mmols) of dibenzyl phosphonate 6 was added drop wise and the mixture stirred for 1 h at 5° C. The reaction was quenched with water, extracted the product with ethyl acetate and organic layers were washed with water and brine. Filtration of the product through a plug of silica gel afforded 0.52 g of the product 7 as brown liquid.

Provenance & Evidence