Diethyl Ether → HCID 21187637, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of n-butyllithium (1.6 M in hexanes, 8.8 ml) and anhydrous ether (20 ml) was stirred at −78° C. under argon and a solution of 2-bromopyridine (1.22 ml) in anhydrous ether (20 ml) added dropwise over 10 minutes. The resulting deep red solution was stirred for 10 minutes and a solution of cyclohexanedione monoethylene ketal (2 g) in tetrahydrofuran (20 ml) then introduced dropwise over 10 minutes. The resulting green suspension was maintained at −78° C. for one hour then warmed to −20° C. and stirred for a further hour, after which a yellow solution had formed. The reaction was quenched with saturated aqueous ammonium chloride (60 ml) and the layers separated. The aqueous was partitioned with dichloromethane (2×80 ml) and combined organics were dried (sodium sulphate) and concentrated in vacuo to give a yellow oil. This was adsorbed onto silica for purification by chromatography eluting with 0-100% ethyl acetate/isohexane to give 8-pyridin-2-yl-1,4-dioxaspiro[4.5]decan-8-ol as a pale yellow solid (1.45 g, 48%).

Provenance & Evidence