Water → HCID 10880940, compound

Participants

Reaction Steps

A solution of n-butyllithium in hexanes (16.8 ml, 2.5 M) was added dropwise to ice-cooled propylene glycol (25 ml) under an atmosphere of nitrogen. When addition was complete the mixture was stirred at room temperature for 15 minutes. A solution of crude 5-(2-bromoethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (10.1 g, prepared as described in Example 3) was added in one portion and the reaction mixture was stirred at room temperature for 42 h. Water (40 ml) was added and the mixture was extracted with ethyl acetate (3×75 ml). The combined organic extracts were washed with water (15 ml), dried over sodium sulphate and the solvent was evaporated in vacuo. The oily residue was submitted to column chromatography on silica gel (200 g) using a mixture of THF and n-heptane (3:7) as eluent. Collecting the proper fractions afforded 4.2 g of 5-(2-(3-hydroxypropyloxy)ethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as an oil. TLC: rf=0.18 (SiO2 ; THF/n-heptane=3:7 ).

Provenance & Evidence