Application
O-allyl-2,2,2-trichloroacetimidate can be used to release allyl groups under mild conditions; used to prepare nitrogen-containing intermediates.
Preparation
Sodium Hydride (0.5 g, 21 mmol) is slurried in anhydrous ether
(20 mL) under a nitrogen blanket. Allyl alcohol (210 mmol) is introduced in ether (30 mL) dropwise with
stirring to the slurry. After 20 min, the homogeneous solution is cooled to 0 °C and Trichloroacetonitrile
(20 mL, 200 mmol) is added over 15 min. The mixture is allowed to warm to 20 °C over 60 min and then
concentrated to a syrup. Pentane (20 mL) containing methanol (0.8 mL, 21 mmol) is added followed by
vigorous shaking, filtration, and concentration of the filtrate and pentane washings (2 × 20 mL). The
product imidate is obtained as a clear liquid (90-97%). No further purification is required. Alternatively, the
imidate can be prepared by using sodium methoxide as a catalyst instead of sodium hydride. Other
procedures for the preparation of allyl trichloroacetimidate have been reported.
