Sodium hydride → (3-Phenoxy-4-fluorobenzyl)-(2,2,3,3-tetramethylcyclopropylmethyl)ether

Participants

Reaction Steps

A solution of 1.9 g of 2,2,3,3-tetramethylcyclopropylmethanol and 4.2 g of 3-phenoxy-4-fluorobenzyl bromide in 20 ml of a 1:1 mixture of toluene/dimethylformamide is added dropwise at 0°-5° C. to 0.9 g of sodium hydride (50% dispersion in mineral oil) in 60 ml of a 1:1 mixture of toluene/dimethylformamide. When the reaction has subsided, the batch is stirred for 16 hours at room temperature and, after the dropwise addition of a saturated solution of ammonium chloride, extracted with toluene. The combined toluene extracts are washed with saturated sodium chloride solution, dried over MgSO4 and concentrated by rotary evaporation. The crude product is chromatographed through a column of 300 g of silica gel (elution with a 95:5 mixture of hexane/ether), affording the title compound of formula ##STR9## in the form of a clear oil with a refractive index of nD24 =1.5300 (compound 1).

Provenance & Evidence