Hydrochloric Acid → 3-(Naphthalen-1-yl)propan-1-ol

3-(1-Naphthyl) acrylic acid (5.00 g) was dissolved in methanol (30 ml) and tetrahydrofuran (50 ml), 10% palladium carbon (2.40 g) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 13 hr. The reaction container was purged with nitrogen, the solution was filtered, and the filtrate was concentrated to give a white solid (5.00 g. The white solid was dissolved in tetrahydrofuran (100 ml), and a tetrahydrofuran-borane.tetrahydrofuran solution (1 mol/l, 27.4 ml) was added dropwise to the mixture under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 18 hr. To the reaction mixture was added water, and 1M aqueous hydrochloric acid solution was added. The mixture was extracted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the object product (4.70 g) as a colorless oil.

1. customThe reaction container was purged with nitrogen
2. filtrationthe solution was filtered
3. concentrationthe filtrate was concentrated
4. customto give a white solid (5.00 g
5. temperaturecooling
6. stirringthe mixture was stirred under ice-
7. temperaturecooling for 1 hr
8. waitfurther at room temperature for 18 hr
9. additionwas added
10. extractionThe mixture was extracted with ethyl acetate
11. washwashed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
12. dry with materialdried over anhydrous magnesium sulfate
13. customThe solvent was evaporated under reduced pressure
14. customThe obtained residue was purified by silica gel column chromatography

ORD 기록

ord-d168bc036e1a45eaaf32c38dea6744f5

출처 데이터셋

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08129361B2