Methyl morpholine oxide → HCID 178492628, compound

Participants

Reaction Steps

To a stirred mixture of {trans-3-(4-methoxyphenoxy)cyclobutyl}methanol (19.8 g, 95.3 mmol), N-methylmorpholine N-oxide (16.7 g, 143 mmol) and powdered 4A molecular sieves (48 g) in methylene chloride (190 ml) was added solid tetrapropylammonium perruthenate (1.67 g, 4.80 mmol) at room temperature under argon atmosphere. On completion, the mixture was filtered through a pad of silica, eluting with methylene chloride (500 ml). The filtrate was evaporated and the residue purified by silica-gel column chromatography {SiO2, 500 g; hexane/ethyl acetate (3/1)} to afford 12.2 g (62%) of trans-3-(4-methoxyphenoxy)cyclobutanecarbaldehyde as white solids: 1H NMR δ9.88 (s, 1H), 6.88-6.65 (m, 4H), 4.75-4.58 (m, 1H), 3.76 (s, 3H), 3.31-3.15 (m, 1H), 2.82-2.61 (m, 2H), 2.54-2.25 (m, 3H).

Provenance & Evidence