Diphenylmethylchlorosilane

Typical Procedure:
A solution of cyclohexylmethanol (3.00 g, 26.3 mmol) in DMF (26 mL) and imidazole (3.934 g, 57.8 mmol) is placed in a three-necked, 100 mL flask fitted with a magnetic stirrer, addition funnel, and a nitrogen inlet. The addition funnel is then charged with diphenylmethylsilyl (DPMS) chloride (6.727 g, 28.9 mmol). Dropwise addition of the DPMS chloride takes 1 h, and after an additional hour of being stirred the reaction is complete (determined by GC). The reaction mixture is then poured into a separatory funnel containing water (100 mL), and the resulting solution is extracted with ether (3 × 200 mL). The individual ether layers are washed with water (150 mL) and saturated brine, combined, dried over Na₂SO₄, and evaporated to give a yellow oil (8.40 g). The oil is fractionally distilled [bp 155 °C (0.3 torr)], yielding the product (7.09 g, Y. 87%).