Cyclohexanol → 5-Cyclohexyloxy-2,2-dimethyl-benzo[1,3]dioxin-4-one

Participants

Reaction Conditions

Reaction Steps

To a cold mixture of 5-hydroxy-2,2-dimethyl-benzo[1,3]dioxin-4-one (1 g, 5.21 mmol) and cyclohexanol (1.98 g, 19.8 mmol) and triphenyl phosphine (2.46 g, 9.38 mmol) in THF in an ice bath was added diisopropyl azodicarboxylate (DIAD) (1.94 g, 9.59 mmol). Resulting mixture was stirred at 0° C. for 15 min and then at rt for 1 h. Reaction mixture was concentrated and the residue was purified by silica gel chromatography (eluting with 50%-100% CH2Cl2 in hexanes) to provide the title compound (0.97 g). 1H NMR (200 MHz, CDCl3): δ (ppm)=7.36 (t, J=8.2 Hz, 1H), 6.60 (d, J=8.6 Hz, 1H), 6.47 (d, J=8.2 Hz, 1H), 4.39 (m, 1H), 1.93-1.37 (m, 10H), 1.69 (s, 6H).

Provenance & Evidence