4-Methoxyphenol → HCID 178472522, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl cis-3-hydroxycyclobutanecarboxylate (1.32 g, 9.20 mmol), 4-methoxyphenol (3.43 g, 27.6 mmol) and triphenylphosphine (3.12 g, 11.9 mmol) in dry THF (25 ml) was added dropwise diethyl azodicarboxylate (2.07 g, 11.9 mmol) in dry THF (5 ml) under argon atmosphere at room temperature. After completion of addition, the mixture was heated to 80° C., maintained at the same temperature for 1 h, and then volatiles removed under reduced pressure. Chromatographic purification of the residue {SiO2, 150 g; hexane/ethyl acetate (20/1)} provided 1.96 g (85%) of ethyl trans-3-(4-methoxyphenoxy)cyclobutanecarboxylate as a colorless oil. 1H NMR δ56.85-6.69 (m, 4H), 4.90-4.80 (m, 1H), 4.18 (q, J=7.0 Hz. 2H), 3.76 (s, 3H), 3.20-3.09 (m, 1H), 2.78-2.62 (m, 2H), 2.5-2.35 (m, 2H), 1.29 (t, J=7.0 Hz, 3H).

Provenance & Evidence