3-Phenylglutaric acid → 3-Phenylpentane-1,5-diol

Temperature

0 °C

3-Phenylglutaric acid (3.39 g, 16.3 mmol) was dissolved in tetrahydrofuran (163 mL) and cooled to 0° C. A 1.0 M tetrahydrofuran solution of borane tetrahydrofuran complex (65 mL, 65 mmol) was added dropwise, and the reaction was allowed to warm to room temperature overnight. The reaction was cooled to 0° C., quenched with methanol slowly, followed by water, and concentrated in vacuo. The resulting solid was stirred with 1N hydrochloric acid for 20 minutes. The solution was extracted into ethyl acetate. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.75-1.86 (m, 2H), 1.86-1.96 (m, 2H), 2.45 (br s, 2H), 2.87-2.95 (m, 1H), 3.39-3.48 (m, 2H), 3.49-3.57 (m, 2H), 7.15-7.22 (m, 3H), 7.25-7.31 (m, 2H).

1. temperatureto warm to room temperature overnight
2. temperatureThe reaction was cooled to 0° C.
3. customquenched with methanol slowly
4. concentrationconcentrated in vacuo
5. extractionThe solution was extracted into ethyl acetate
6. dry with materialThe combined organic layers were dried (magnesium sulfate)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by column chromatography on silica gel
10. washeluting with ethyl acetate

ORD record

ord-ce83215e1364442e860068d013e68d81

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08053455B2