Water → HCID 22261369, compound

Participants

Reaction Conditions

Reaction Steps

In a nitrogen atmosphere, 1.84 ml (22.8 mmol) of pyridine was added to 30 ml of dichloromethane at 0° C., and further, 1.33 ml (14.3 mmol) of phosphorus oxychloride was added, followed by stirring for 15 minutes. To this reaction solution, a solution having 4-t-butyl-5-[4-(5-trifluoromethyl-3-isoxazolyl)-3-hydroxyphenyl]-3,3-dimethyl-2,3-dihydrofuran (compound 13)) (1.44 g, 3.78 mmol) dissolved in dichloromethane (12 ml), was dropwise added, followed by stirring at 0° C. for 2 hours. Further, the reaction solution was gradually returned to room temperature and stirred for 1 day. The reaction solution was again cooled to 0° C., and 3.68 ml (45.5 mmol) of pyridine was added. Further, 3.20 ml (47.3 mmol) of ethylene cyanohydrin was added, and the mixture was gradually returned to room temperature and stirred for 1 day. The reaction solution was put into pure water (50 ml) and extracted with ethyl acetate (50 ml). The aqueous layer was again extracted with ethyl acetate (50 ml), and the extract was put together with the previous organic layer, followed by washing with pure water (100 ml×3). The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain the desired phosphoric acid 5-(3-t-butyl-4,4-dimethyl-4,5-dihydrofuran-2-yl)-2-(5-trifluoromethylisoxazol-3-yl)phenylester bis-(2-cyanoethyl)ester (compound (15)) as a slightly yellow oily substance (2.10 g, 3.70 mmol, 98.1%).

Provenance & Evidence