Acetone → 2-(4-Aminophenyl)propan-2-ol

Temperature

-78 °C

To a −78° C. solution of compound 134 (1 g, 3.95 mmol) in ether (20 mL) was added sec-BuLi (1.4 M in hexanes, 0.62 g, 9.67 mmol). The resulting solution was stirred for 30 min at −78° C., followed by addition of acetone (0.91 g, 15.81 mmol) dropwise at −78° C. The reaction mixture was warmed to room temperature overnight. The reaction mixture was partitioned between water and ether and the layers were separated. The aqueous layer was re-extracted with ether. The ether layers were the combined and concentrated in vacuo to yield crude 135 (0.33 g, 55.9%) which was used in the next step without further purification.

1. temperatureThe reaction mixture was warmed to room temperature overnight
2. customThe reaction mixture was partitioned between water and ether
3. customthe layers were separated
4. extractionThe aqueous layer was re-extracted with ether
5. concentrationconcentrated in vacuo

ORD record

ord-051cd53402dd4d2ca356d051c7642cbc

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541423B2