77070-73-6

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 823-45-0 2-(hydroxymethylene)cyclohexanone 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 14444-77-0 diethyl phenyl orthoformate 
• 1478-41-7 diethoxycarbonium fluoroborate 
• 108-94-1 cyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 

Downstream Products

• 171193-57-0 1-formyl-2-methyl-2-cyclohexanol diethyl acetal 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 89186-00-5 1-formyl-2-cyclohexanol diethyl acetal 
• 2305-78-4 4,5,6,7-tetrahydro-2,1-benzisoxazole 
• 171193-58-1 2-diethoxymethyl-1-ethylcyclohexanol 
• 54625-15-9 2-methylcyclohex-1-ene-1-carbaldehyde 
• 1254984-78-5 2-diethoxymethyl-1-prop-2-ynylcyclohexanol 

Relevant academic research and scientific papers

Reaction of Enamines with Acetals or Trialkyl Orthoformates Activated by Lewis Acids

Enamines, prepared readily from various carbonyl compounds, react with acetals or trialkyl orthoformates in the presence of Lewis acids such as BF3.OEt2 to give corresponding β-alkoxy carbonyl compounds or α-dialkoxymethyl carbonyl compounds in good yields.The reaction of dienamines with acetals or trialkyl orthoformates also selectively gives corresponding β,χ-unsaturated α-(α-alkoxyalkyl) carbonyl compounds or β,χ-unsatureted α-dialkoxymethyl carbonyl compounds in good yields.

Preparation d'acetals fonctionnels

Functional acetals can be prepared either by reaction of functional organomagnesium compounds with the mixed orthoformate C6H5O-CH()C2H5)2 or by reaction of carbonyl compounds with the acetylenic lithium compounds Li-CC-(CH2)n-CH(OC2H5)2 (n=0,1).

NEW SYNTHESIS OF β-KETO ACETALS

Enamines derived from ketones or aldehydes react smoothly with trialkyl orthoformates in the presence of Lewis acids to give β-keto acetals in good yields.

A Procedure for Diethoxymethylation of Ketones

Reaction of a number of ketones with diethoxycarbenium fluoroborate in the presence of N,N-diisopropylethylamine at low temperature in methylene chloride results in a preparatively useful conversion to α-(diethoxymethyl) ketones.The method is compatible with arene, nitrile, chloride, and ester functional groups.With unsymmetrically substituted ketones, it is regioselective for the less substituted α-position.In favorable cases α,α'-dialkylation occurs.Conjugated ketones react normally at the saturated position adjacent to the carbonyl group.The mechanism of the reaction is considered.

Chemistry of enol ethers. LI. Reaction of vinyl silyl ethers with orthoformic esters

The silyl ethers of enolic forms of ketones react with orthoformates in the presence of zinc chloride at catalyst to form β-ketoacetals.The analogous reaction with the silyl ethers of enolic forms of aldehydes leads to the formation of the tetraacetals of 1,3-dialdehydes.