ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > t-Butyl (E)-4-Iodo-2-methyl-2-butenoate
t-Butyl (E)-4-Iodo-2-methyl-2-butenoate
t-Butyl (E)-4-Iodo-2-methyl-2-butenoate Basic information
- Product Name:
- t-Butyl (E)-4-Iodo-2-methyl-2-butenoate
- Synonyms:
-
- t-Butyl (E)-4-Iodo-2-methyl-2-butenoate
- 2-Butenoic acid, 4-iodo-2-methyl-, 1,1-dimethylethyl ester
- t-butyl γ-iodotiglate
- CAS:
- 53689-87-5
- MF:
- C9H15IO2
- MW:
- 282.12
- Mol File:
- 53689-87-5.mol
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t-Butyl (E)-4-Iodo-2-methyl-2-butenoate Chemical Properties
- Boiling point:
- 80 °C/0.005 mmHg
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t-Butyl (E)-4-Iodo-2-methyl-2-butenoate Usage And Synthesis
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.