Potassium Hydroxide → HCID 57467212, compound

Tert-butyl [1-(4-chlorobenzyl)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate (180 mg, 0.464 mmol, prepared analogously to tert-butyl [1-(3,4-dichlorobenzyl)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate, cf. Example 34.2 and potassium hydroxide (1.4 g, 25 mmol) were suspended in acetonitrile (4 mL). After stirring the two phase system for 45 min at room temperature the reaction mixture was cooled to −15° C. and a solution of 2-chloro-2,2-difluoro-1-phenylethanone (442 mg, 2.32 mmol) in acetonitrile (1 mL) was added dropwise over 30 min. The reaction mixture was warmed to room temperature and then heated at 80° C. for 2 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined extracts were dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane, silica gel). Yield: 30 mg (0.069 mmol, 15%).

1. temperaturewas cooled to −15° C.
2. temperatureThe reaction mixture was warmed to room temperature
3. temperatureheated at 80° C. for 2 h
4. temperatureThe reaction mixture was cooled to room temperature
5. extractionThe aqueous layer was extracted with ethyl acetate
6. dry with materialThe combined extracts were dried (MgSO4)
7. concentrationconcentrated in vacuo
8. customThe crude product was purified by flash chromatography (dichloromethane, silica gel)

ORD record

ord-7e5958f0834e42c691765cb79331bd70

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563617B2