Ethyl acetate hexane → HCID 178455821, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of potassium tert-butoxide (7.85 g, 70 mmol) in THF (50 ml) was cooled to -78° C. under argon atmosphere. To this was added a solution of methyl (diazomethyl)phosphonate (J. Org. Chem. 1979, 44, 4997) (12.5 g, 70 mmol) in THF (100 ml), followed after 0.5 h by a solution of trans-3-(4-methoxyphenoxy)cyclobutanecarbaldehyde (12.1 g, 58.7 mmol) in THF (100 ml) at the same temperature. The resulting solution was stirred at -78° C. for 3 h and then maintained at room temperature for another 8 h. The reaction was quenched with water (300 ml) and the aqueous mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine (200 ml), dried (MgSO4) and concentrated in vacuo to give yellow solids. Silica-gel column chromatography of the solids {SiO2, 800 g; hexane/ethyl acetate (9/1)} of the solids afforded 6.49 g (55%) of {trans-3-(4-methoxyphenoxy)cyclobutyl }ethyne as white solids: 1H NMR δ6.84-6.70 (m, 4H), 4.92-4.82 (m, 1H), 3.76 (s, 3H), 3.20-3.03 (m, 1H), 2.64-2.40 (m, 4H), 2.19 (s, 1H).

Provenance & Evidence