A Convenient Synthesis of α-Tributylstannyl Esters

References

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• Rathke , M. W. and Sullivan , D. F. 1973 . Synth. Commun. , 3 : 67 Addition of tributyltin chloride to the ester enolate obtained from lithium dicyclohexylamide and ethyl isobutyrate, followed by a non-aqueous work-up, gave only the C-stannylated product. In contrast, silylation of the same ester enolate is known to give 99% of the O-silylated product:
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• 1H NMR spectra were taken in deuterated chloroform using tetramethylsilane as internal standard. IR spectra were taken neat. 1: 1H NMR δ 1.83 (s, 2H), 1.4 (s, 9H), 1, 8–0. 7 (m, 27H); IR 1690 cm−1. 2: 1H NMR δ 4. 05 (q, 2H), 1.92 (s, 2H), 1.8–0.7 (m, 30H); IR 1700 cm−1. 3: 1H NMR δ 3.6 (s, 3H), 1.9 (s, 2H), 1. 8–0.7 (m, 27H); IR 1720 cm−1. 4: 1H NMR δ 4.1 (q, 2H), 2.4 (q, 1H), 1, 8–0.7 (m, 33H); IR 1700 cm−1. 5: 1H NMR δ 1 (q, 2H), 1.4 (s, 6H), 1.8–0.7 (m, 30H); IR 1700 cm−1. 6: 1H NMR δ 3.6 (s, 3H), 1.4 (s, 6H), 1.8–0.7 (m, 27H); IR 1700 cm−1. 7: 1H NMR δ 4.1 (q, 2H), 2.3 (m, 1H), 1.8–0.7 (m, 41H); IR 1700 cm-1
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