Methyl morpholine oxide → (E)-2-Fluoro-3-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enal

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Reaction Steps

A mixture of (E)-2-fluoro-3-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-en-1-ol (Intermediate 7, 1.01 g, 3.04 mmol), NMO (0.89 g, 7.60 mmol), TPAP (catalytic amount), and 4 Å molecular sieves (200 mg) in CH2Cl2—CH3CN (40 mL, 8 mL) was stirred at ambient temperature for 45 min. The mixture was loaded onto a pad of silica gel and eluted with 10% EtOAc-hexane to give the tide compound as a pale yellow solid (890 mg, 89%).

Provenance & Evidence