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

Temperature

20 °C

To a solution of 2.5 M 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-methoxycyclohexane (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 1 N hydrochloric acid (50 ml). This aqueous extract was washed with ether (20 ml) and then treated with 2 M sodium hydroxide solution (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 afforded (±)-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 1 N hydrochloric acid (50 ml)
4. extractionThis aqueous extract
5. washwas washed with ether (20 ml)
6. additiontreated with 2 M sodium hydroxide solution (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-04e5130fb495498c887d3298cf588c53

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05104883