Hexane → (+)-2-Methoxy-1-(pyrid-3-yl)cyclohexanol

Temperature

20 °C

To a solution of 2.5M n-butyllithium in hexane (13.2 ml, 33 mmol) at -78° C. was added diethyl ether (15 ml) followed by a solution of 3-bromopyridine (4.7 g, 30 mmol) in ether (90 ml) over a period of 10 minutes. After 1 hour at -78° C. a solution of (+)-2-methoxycyclohexanone (3.84 g, 30 mmol) in ether (20 ml) was added dropwise during 10 minutes. After 2 hours at -78° C. and 30 minutes at 0° C. the reaction mixture was warmed to 20° C. and then poured onto ice (150 g). The mixture was extracted with ether (2×50 ml) and then the combined organic extracts were extracted with hydrochloric acid (1M, 50 ml). This aqueous extract was washed with ether (20 ml) and then treated with sodium hydroxide solution (2M, 25 ml) and extracted with ether (3×100 ml). The organic extracts were combined, washed with brine then dried over anhydrous sodium sulphate. Concentration in vacuo gave (+)-2-methoxy-1-(pyrid-3-yl)cyclohexanol (5.0 g, 24 mmol) as a 4:1 mixture of cis and trans isomers;

1. additionpoured onto ice (150 g)
2. extractionThe mixture was extracted with ether (2×50 ml)
3. extractionthe combined organic extracts were extracted with hydrochloric acid (1M, 50 ml)
4. extractionThis aqueous extract
5. washwas washed with ether (20 ml)
6. additiontreated with sodium hydroxide solution (2M, 25 ml)
7. extractionextracted with ether (3×100 ml)
8. washwashed with brine
9. dry with materialthen dried over anhydrous sodium sulphate
10. concentrationConcentration in vacuo

ORD record

ord-9694360209064420bfac1f8165310dd3

Source dataset

uspto-grants-1994_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05276046