Ozone → (+/-)-5-(3-Pyridyl)-1,3-pentanediol

A mixture of ozone in air was passed through a solution of (±)-6-(3-pyridyl)-hex-1-en-4-ol (1.38 g) in methanol (70 ml) at 0° C. for 2 hours. The solution was flushed with nitrogen for 1 hour then sodium borohydride (2 g) was added portionwise. The mixture was stirred at room temperature for 20 hours and then concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with methanol:dichloromethane (1:19) and the required fractions concentrated under reduced pressure. Ethyl acetate (25 ml) and aqueous potassium tartrate solution (1 M, 25 ml) were added to the residue and the mixture stirred rapidly for 2 hours. The phases were separated and the aqueous phase extracted with ethyl acetate (10×25 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the sub-title compound as an oil (1.20 g).

1. customThe solution was flushed with nitrogen for 1 hour
2. additionsodium borohydride (2 g) was added portionwise
3. concentrationconcentrated under reduced pressure
4. customThe residue was purified by column chromatography over silica eluting with methanol:dichloromethane (1:19)
5. concentrationthe required fractions concentrated under reduced pressure
6. additionEthyl acetate (25 ml) and aqueous potassium tartrate solution (1 M, 25 ml) were added to the residue
7. stirringthe mixture stirred rapidly for 2 hours
8. customThe phases were separated
9. extractionthe aqueous phase extracted with ethyl acetate (10×25 ml)
10. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure

ORD record

ord-feb33abec34844d38e1c3eb36b24a053

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05977105