反应详情

To a solution of 3-amino-5-ethoxy-4-iodo-benzoic acid methyl ester (0.18 g, 0.56 mmol, 1.0 equiv) in THF (5 mL) at 0° C. under Ar was slowly added diisobutylaluminium hydride (2.8 mL, 2.80 mmol, 5.0 equiv, 1 M solution in THF) over a time period of 30 min, the cooling bath removed on completion of addition and the reaction allowed to reach rt. After 2 h, the excess hydride was quenched by cautious addition of a sat. solution of potassium sodium tartrate (50 mL). The solidified mixture was extracted with hot THF, the combined organic phases concentrated by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1) providing 0.056 g (34%) of the title compound. 1H NMR (250 MHz, CDCl3): δ 1.47 (t, J=7.0 Hz, 3H), 4.08 (q, J=7.0 Hz, 2H), 4.23 (br s, 2H), 4.58 (d, J=6.0 Hz, 2H), 6.23 (s, 1H), 6.42 (s, 1H). MS (EI): 293.0 [M]+.

1. customat 0° C.
2. customover a time period of 30 min
3. customthe cooling bath removed on completion of addition
4. customto reach rt
5. customthe excess hydride was quenched by cautious addition of a sat. solution of potassium sodium tartrate (50 mL)
6. extractionThe solidified mixture was extracted with hot THF
7. concentrationthe combined organic phases concentrated by evaporation under reduced pressure
8. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1)