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Solutions for Condensations and Alpha Substitutions of Carbonyl Compounds
67 continued
OR
N
OEt
O
CH3
O
CH3
O
Cl Ph
O
H Ph
O
H3C
O
EtO
O
H3O+
HO–
EtO–
EtO–
O
Ph
O
O
Ph
O O
O O
(d) mixed Claisen
+
+
(e) mixed aldol
+
(f) enamine acylation or mixed Claisen
+
O
EtO Ph
O
+
H3O+
OR
EtO–
In practice, the mixed Claisen reactions starting from a 
ketone enolate plus an ester will give a considerable 
amount of aldol self-condensation.
H
O
O
CH2CH2CH2CH3
O
O
Ph
O O
OCH3
O
CH2CH2CH2CH3
O
CH3
CH3Ph
+ CO2 
+ CH3CH2OH
(c)
(i)
+ CO2 + CH3OH
(h)
(d)
(f)(e) (g)
O
O O
initial product
O
O
O
OEtO
initial product
O
Br
(a) (b) COOH
+ CHI3
68
after acid workup
583