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2-Methylcyclopentane-1,3-dione is an efficient synthon for the synthesis of (±)-α-cuparenone. The alkylation of 2-methylcyclopentane-1,3-dione (A) with 2-(1-naphthyl)ethyl bromide gives only the O-alkylation product. Mixtures of C- and O-alkyl derivatives are obtained. Michael addition of 2-methylcyclopentane-1,3-dione to methyl vinyl ketone in water gives 2-methyl-2-(3-oxo- butyl)-1,3-cyclopentanedione (3), an important intermediate of natural product chemistry. 2-Methylcyclopentane-1, 3-dione is an efficient synthon for the synthesis of (±)-α-cuparenone.
Joseph P. John,; S. Swaminathan,; P. S. Venkataramani. 2-Methylcyclopentane-1,3-Dione. Organic Syntheses. year of publication , volume issue , pg no.
Victor J. Grenda,; Glenn W. Lindberg,; Norman L. Wendler,; Seemon H. Pines. A convenient synthesis of 2-methylcyclopentane-1,3-dione . J. Org. Chem. 1967, 32 (4), 1236-1237.
Valuable intermediate for steroid synthesis. For a review, see: Synthesis, 477 (1989). Condensation with methyl vinyl ketone and proline-catalyzed asymmetric aldol cyclization of the product gives a diketone useful in steroid and prostaglandin synthesis: Org. Synth. Coll., 7, 363 (1990):
Hazard Statements: H500
May form combustible dust concentrations in air