Flippin, Lee A.; Berger, Jacob; Parnes, Jason S.; Gudiksen, Mark S. published the artcile< Effect of the Substitution Pattern on Reactions of Methoxylated Araldehyde 2,4-Dimethyl-3-pentylimines with Organolithium Reagents>, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde, the main research area is methoxyphenylmethylenepentanamine butylation phenylation; substitution effect lithiation araldehyde methylpentylimine; metalation regioselective araldimine; imine methoxybenzaldehyde lithiation substitution effect.
Araldehyde imines, e.g., N-[(methoxyphenyl)methylene]dimethyl-3-pentanamines I (R, R1, R2 = H, OMe) reacted with BuLi via facile nucleophilic aromatic substitution to give benzaldehydes II. Exceptions to this trend were observed when the araldimine substrate contained methoxy groups at both C-2 and C-5. Thus, the 2,5-dimethoxy analog of I reacted with BuLi – followed by MeI quench and acid hydrolysis – to give a complex aldehyde mixture derived from metalation and SNAr processes, e.g. 3,6-dimethoxy-2-methylbenzaldehyde and 2-butyl-5-methoxybenzaldehyde, whereas the 2,4,5-trimethoxy analog of I under identical conditions, gave exclusive metalation and electrophilic capture at C-6 to give 3,4,6-trimethoxy-2-methylbenzaldehyde in 83% yield. Araldehyde 2,4-dimethyl-3-pentylimines that cannot undergo an SNAr reaction are potential candidates for directed metalation reactions although this usage is limited by occasional unwanted side-reactions, lack of selectivity or reactivity, and unpredictability.
Journal of Organic Chemistry published new progress about Alkylation. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde.
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem