Benzyl Alcohol → HCID 131731397, compound

A solution of 5-bromopentanoic acid (1.00 g, 5.52 mmol) and benzyl alcohol (0.286 mL, 2.76 mmol) in methylene chloride (14 mL) was treated sequentially with N,N′-diisopropylcarbodiimide (0.523 g, 4.14 mmol) and 4-dimethylaminopyridine (43.9 mg, 0.359 mmol). The solution was allowed to stir at room temperature. A precipitate formed within 1 minute of the addition of the 4-dimethylaminopyridine. After −65 h, the reaction mixture was filtered, the solid was washed with CH2Cl2 and the filtrate was washed with 20 mL portions of 1N HCl, sat NaHCO3 and brine and dried over Na2SO4. The solution was filtered and concentrated to yield a nearly colorless liquid along with a solid (DIC urea). The material was taken up in 1/1 MTBE/heptane to yield a solution with a white precipitate. The mixture was filtered and concentrated and the crude material was purified by flash chromatography (75 g silica gel; 5-10% MTBE/hept) to yield the title compound (0.69 g, 92%) as a colorless liquid. HPLC purity>95% (ret. time, 4.73 min).

1. waitAfter −65 h
2. filtrationthe reaction mixture was filtered
3. washthe solid was washed with CH2Cl2
4. washthe filtrate was washed with 20 mL portions of 1N HCl
5. dry with materialdried over Na2SO4
6. filtrationThe solution was filtered
7. concentrationconcentrated

ORD record

ord-54c4c4c123f848978ea255912e429510

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145438B2