Diazomethane → Methyl 5-methyl-4-hexenoate

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Freshly prepared diazomethane in ether was added to an ice-cooled solution of 5-methyl-4-hexenoic acid (4.5 g, 35.16 mmol) in ether (10 mL) until the solution became slightly yellow in color. The solvent was then evaporated under vacuum to afford the title product as a colorless liquid in near quantitative yield (4.90 g). This product was used in the next reaction step without further purification. 1H NMR (CDCl3) δ 1.62 & 1.68 [2s, 6H, C(CH3)2 ], 2.30 [m, 4H, (CH2)2 ], 3.69 (s, 3H, COOCH3) and 5.07 (t, 1H, CH).

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