4-Methyl-2-methylene valeric acid → 2-[(Acetylthio)methyl]-4-methylpentanoic acid

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Reaction Conditions

Reaction Steps

A mixture of 4-methyl-2-methylenepentanoic acid (5.0 g) and thioacetic acid (25 mL) was heated at 95° C. under argon for 3 days. The excess thioacetic acid was evaporated and the residual oil was dissolved in ethyl acetate (40 mL) and extracted with saturated NaHCO3 (3×40 mL). The combined NaHCO3 extracts were combined and acidified at 0° C. to pH 2 with 1M HCl. The aqueous layer was extracted with CHCl2 (3×40 mL), the combined organic phases were dried (MgSO4) and evaporated to give 3.0 g of 4-methyl-2-acetylthiomethyl-pentanoic acid; 1H NMR (80 MHz, CDCl3) δ 0.95 (d, J=8.0, 6H), 1.20-1.90 (m, 4H), 2.35 (s, 3H), 2.50-3.20 (m, 3H), 6.7 (br s, 1H).

Provenance & Evidence