反应详情

A solution of Boc-pyrrole-OH (8)(2.9 g 12 mmol), 4-(bromomethyl)benzoic acid phenacyl ester (22) (4 g, 12 mmol) and diisopropylethylamine (3.0 ml, 16.8 mmol) in 60 ml of DMF were stirred at 50° C. for 6 hours. The solution was cooled and partitioned between 400 ml of water and 400 ml of ethyl ether. The ether layer was washed with (2×200 ml each) of 10% citric acid, brine, saturated sodium bicarbonate and brine. The organic phase was dried with sodium sulfate and concentrated in vacuo to yield compound 38 as light white foam which was used without further purification (5.4 g, 97% yield). TLC (2:3 hexane/ethyl acetate) Rf 0.6; 1H NMR (DMSO-d6) δ 9.14 (s, 1H), 8.03 (m, 4H), 7.67 (m, 1H), 7.55 (m, 4H), 7.13 (s, 1H), 6.72 (d, 1H, J=1.5 Hz), 5.74 (s, 1H), 5.32 (s, 1H), 3.79 (s, 3H), 1.42 (s, 9H); 13C NMR (DMSO-d6) δ 193.2, 165.5, 160.4, 153.2, 143.1, 134.5, 130.1, 129.5, 128.3, 128.2, 123.8, 120.3, 118.8, 108.2, 79.1, 67.7, 64.6, 36.7, 28.6.

1. temperatureThe solution was cooled
2. custompartitioned between 400 ml of water and 400 ml of ethyl ether
3. washThe ether layer was washed with (2×200 ml each) of 10% citric acid, brine, saturated sodium bicarbonate and brine
4. dry with materialThe organic phase was dried with sodium sulfate
5. concentrationconcentrated in vacuo