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Printed Magazine "TCIMAIL" > TCIMAIL Back Numbers 2016 >

Alkylation Reagents for Ester Synthesis

No.168(January 2016)
D4587
N,N'-Diisopropyl-O-methylisourea (1)
E1058
O-Ethyl-N,N'-diisopropylisourea (2)
T3123
O,N,N'-Triisopropylisourea (3)
B4178
O-tert-Butyl-N,N'-diisopropylisourea (4)
B4480
O-Benzyl-N,N'-diisopropylisourea (5)
O-Alkylisoureas (1) to (5) are convenient and useful esterification reagents for the direct alkylation of carboxylic acids. For example, Golding et al. have reported the esterification of 1-cyclobutenecarboxylic acid using 1, affording the corresponding methyl ester.1)
Moreover, Linclau et al. have reported the microwave-accelerated esterification of carboxylic acids using 4 and 5, affording the corresponding esters in excellent yields within several minutes.2)
For another example, the esterification reaction using 2 and 3 also has been reported as below.3)

References

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