Sodium hydride → 5-Octyl-2-(4-(5,5-difluoro-5-(perfluorobutoxyethoxy) pentoxy)phenyl)pyrimidine

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Reaction Conditions

Reaction Steps

Using essentially the procedure of Example 97, a flask was charged with sodium hydride (0.4 g of a 60 weight % suspension in mineral oil, 1.65 mmoles) and dimethyl formamide (5 mL). With stirring, 5-octyl-2-(4-hydroxyphenyl)pyrimidine (0.33 g, 1.1 mmole) was slowly added to the resulting mixture to control the hydrogen evolution. The mixture was stirred at room temperature for 30 minutes, 5,5-difluoro-5-(perfluorobutoxyethoxy)-1-pentanol toluenesulfonate (0.6 g, 0.95 mmoles) was then added, and the mixture was heated at 100° C. for one hour. The mixture was worked up essentially as in Example 99 and was distilled using a Kugelrohr apparatus (b.p. approximately 180°-200° C. at 0.4 torr). The product yield was 5.72 g (structure confirmed by 1H and 19F nuclear magnetic resonance spectroscopy).

Provenance & Evidence