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

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)+.

1. additionOn completion of the addition the flask
2. customwas equipped with a condenser
3. temperaturethe mixture heated under nitrogen
4. temperatureto reflux in an oil bath for ten hours
5. customThe reaction was quenched by the cautious drop wise addition of methanol (60 mL)
6. concentrationThe resulting mixture was concentrated to an oil which
7. dissolutionwas then dissolved in ethyl acetate (150 mL)
8. additiontreated with 1N HCl
9. washThe resulting organic phase was washed with brine (4×50 mL)
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated
13. concentrationre-concentrated
14. filtrationcollected by vacuum filtration
15. washThe cake was washed with hexane (50 mL)
16. customthen dried under vacuum

ORD record

ord-a491f1d9c7d5415b9995bae38ab5feeb

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691938B2