Ethyl 2-methyl-2-(4-nitrophenyl)propanoate → 2-Methyl-2-(4-nitrophenyl)propan-1-ol

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Reaction Steps

To a solution of the product from Example 194A (12.32 g, 55.2 mmole) in anhydrous THF (300 mL) at room temperature under nitrogen was added dropwise via cannulae 1M BH3 in THF (200 mL) over ten and one half minutes. On completion of the addition the flask was equipped with a condenser and the mixture heated under nitrogen to reflux in an oil bath for ten hours before cooling to room temperature. The reaction was quenched by the cautious drop wise addition of methanol (60 mL). The resulting mixture was concentrated to an oil which was then dissolved in ethyl acetate (150 mL) and treated with 1N HCl and allowed to stir at room temperature for one hour. The resulting organic phase was washed with brine (4×50 mL), dried over MgSO4, filtered and concentrated. The residue was taken up in toluene (25 mL) and re-concentrated. The oily solid was suspended in hexane (50 mL) and collected by vacuum filtration. The cake was washed with hexane (50 mL) then dried under vacuum to provide the title compound (9.55 g, 89% yield) as a light orange solid. MS (DCI+) m/z @ 213.1 (M+NH4)+.

Provenance & Evidence