Dibutyltin dichloride → HCID 59314171, compound

Participants

Reaction Steps

A 10 mL microwave reaction vessel is charged with 2-amino-indan-2-carboxylic acid ethyl ester (500 mg, 2.44 mmol) and dry tetrahydrofuran (THF, 5 mL). A stirring bar is added and stirring is initiated. After dissolution, 2,3-dihydro-1-benzofuran-7-carbaldehyde (361 mg, 2.43 mmol) is added. Stirring is continued. Phenylsilane ([694-18-1], 0.61 mL, 4.87 mmol) and dibutyltin dichloride (53 μL, 244 μM) are added. The reaction vial is crimped sealed and placed in a Smith Microwave Apparatus. The pre-stir time is set to 10 sec. Heating is set at 100° C. for 10 min. The contents of the reaction vial are transferred to a round bottom flask and evaporated by pumping to a constant weight yields 1.56 g of light yellow oil. This material is dissolved in DCM (10 mL) and applied to an ISCO Companion that is fitted with a 40 g Cartridge (silica). The column is eluted with 5% EtOAc/heptanes for 3 column volumes followed by a linear gradient to 50% EtOAc/heptanes over 10 column volumes and then 90% EtOAc/heptanes for 2 column volumes. 14 mL fractions of UV active eluent are collected. Fractions 7 to 11 are combined and evaporated by pumping to constant weight yields 0.59 g of white solid material (0.52 g, 63%).

Provenance & Evidence