反应详情

To tert-butyl 4-acetylbenzoate (3.33 g) in a tetrahydrofuran (23 ml) solution, (−)-B-chlorodiisopinocampheylborane in a 65% hexane solution (11.2 ml) was added dropwise under ice cooling, then the mixture was stirred at that temperature for 1.5 hours. The reaction solution was concentrated, and the residue was diluted by diethyl ether. To the thus solution obtained, diethanolamine (4.3 ml) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The precipitates were removed by filtration, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=9/1 to 4/1) to obtain the title compound (3.47 g).

1. concentrationThe reaction solution was concentrated
2. additionthe residue was diluted by diethyl ether
3. customTo the thus solution obtained
4. stirringthe mixture was stirred at room temperature for 2 hours
5. customThe precipitates were removed by filtration
6. concentrationthe filtrate was concentrated
7. customThe residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=9/1 to 4/1)