Year: 2025
Type: other
Abstract: Procedure (Note 1) A. 3-phenyl-propionaldehyde (2).A glass cannula apparatus (Note 2, Figure 1A) is secured in place with the stopcock between the two flasks open.The transfer flask is equipped with a septum and connected to a nitrogen/vacuum manifold with a bubbler via a 21 G needle.The receiving flask is equipped with a 1.5 cm × 0.5 cm magnetic stir bar and a septum with a temperature probe and an external bubbler connected via a 21 G needle.Under vacuum, the glass cannula apparatus is flame dried, and it is placed under a nitrogen atmosphere for the course of the reaction.The receiving flask is charged with 0.18 mL 3-phenylpropanoic acid ethyl ester (1) (1.00 equiv, 1.00 mmol) and 10.0 mL dichloromethane to create a homogeneous, colorless solution (Note 3).A flame dried, 25 mL conical flask equipped with a rubber septum and connected to a nitrogen/vacuum manifold with an 18 G needle is under a nitrogen atmosphere.The flask is charged with 2.4 mL dicholormethane and 0.27 mL diisobutylaluminum hydride (DIBAL) (1.5 equiv, 1.5 mmol) (Note 4) which is thoroughly mixed by swirling the flask.The transfer flask is charged with the DIBAL solution (Figure 1B).The glass cannula apparatus is immersed in a dry ice-acetone bath for 10 min until the internal temperature stabilizes at -78 °C or lower.The solution in the receiving flask is stirred at a rate of 450 rpm (Figure 1C, Note 5).The transfer of DIBAL solution is initiated by closing the stopcock connecting the two flasks and the gas outlet of the bubbler on the nitrogen manifold (the manifold is not open stoltz@caltech.
Source: Organic Syntheses
Authors: Kaylin N. Flesch, Tyler J. Fulton, Nathan Hart, Brian M. Stoltz*
Institution: California Institute of Technology
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4411448865