Sodium Bicarbonate → 2-Methyl-propane-2-sulfinic acid 1-[4-(tert-butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexyl]-methylideneamide

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Reaction Steps

3.20 g (10.3 mmol) of 4-(tert-Butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexanecarbaldehyde (71) were dissolved using 25 ml of anhydrous THF. 1.31 g (10.8 mmol) of 2-methyl-2-propanesulfinamide and 4.32 ml (20.6 mmol) of titanium (IV) ethoxide were added and the mixture heated for 4 h at reflux. The reaction mixture was poured into 75 ml of a saturated aqueous solution of NaHCO3 and the precipitate removed by filtration. The filtrate was extracted three times using 50 ml of ethyl acetate each. The organic layer was dried using MgSO4 and evaporated to yield 3.90 g of 72. Rt=1.02 min (Method Q).

Provenance & Evidence