Acetaldehyde → Cinnamaldehyde

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Reaction Steps

As shown in Scheme 1, benzaldehyde derivative 1-1 can be reacted with acetaldehyde in the presence of either an acid or a base catalyst to afford cinnamic aldehyde 1-2. Reaction of cinnamic aldehyde 1-2 with an organometallic compound such as a Grignard reagent R8MgX1 [wherein X1 is halo such as Cl or Br], followed by oxidation of the intermediate alcohol to ketone and by reduction of the C═C bond to a C—C single bond under a hydrogenation condition (for example, in the presence of Pd/C catalyst), affords ketone 1-3. Reaction of ketone 1-3 with amine 1-4 under reductive amination condition (such as in the presence of a borohydride reducing reagent) affords compound 1-5.

Provenance & Evidence