Dimethyl Sulfoxide → HCID 67485750, compound

Participants

Reaction Steps

To a solution of catacol (0.5 g, 4.54 mmol), triphenylphosphine (1.79 g, 6.8 mmol) and cyclopenylmethanol (0.68 g, 6.8 mmol) in THF (5 ml) DIAD (1.37 g, 6.8 mmol) is added drop wise over a period of 10-15 min at 0° C. The reaction mixture stirred at r.t. for 18 h, quenched with brine (5 ml), extracted in EtOAc (2×20 ml), and dried over Na2SO4. Solvent was evaporated under reduced pressure and crude product. To a solution of 2-Cyclopentylmethoxy-phenol (0.1 g, 0.52 mmol) and 2-bromoisobutyrate ethyl ester (0.15 g, 0.78 mmol) in DMSO (2 ml) Cs2CO3 (0.25 g, 0.78 mmol) was added and heated at 60° C. for 4 h. The reaction mixture was cooled to r.t. and poured on 10 ml of water, extracted in EtOAc (2×20 ml) dried over Na2SO4. Solvent was removed under reduced pressure to yield 2-(2-Cyclopentylmethoxy-phenoxy)-2-methyl-propionic acid ethyl ester (0.1 g, 63%) which was hydrolysed to give 2-(2-Cyclopentylmethoxy-phenoxy)-2-methyl-propionic acid using method Typical Example (A1-II).

Provenance & Evidence