t-Butyl (E)-4-Iodo-2-methyl-2-butenoate

Reactivity Profile

t-Butyl (E)-4-Iodo-2-methyl-2-butenoate could be used in egioselective annulations; methyl vinyl ketone equivalent.

Synthesis

Treatment of Chloroacetaldehyde with the phosphorane shown in eq 1 followed by halogen exchange with Sodium Iodide/acetone affords t-Butyl (E)-4-Iodo-2-methyl-2-butenoate in 76% overall yield.

References

1. (a) Gawley, R. E. S 1976, 777; (b) Hill, K. H. Ph.D. Thesis, University of Texas, Austin, TX, 1972.
2. (a) Stotter, P. L.; Hill, K. A. TL 1975, 16, 1679. (b) Stotter, P. L.; Hill, K. A. JACS 1974, 96, 6524.
3. Weinstock, J. JOC 1961, 26, 3511.