Sodium Methoxide → Methyl 5-((2-propylpentyl)oxy)furan-2-carboxylate

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Reaction Steps

2-Propylpentyl 5-((2-propylpentyl)oxy)furan-2-carboxylate (0.62 g, 1.76 mmol), NaOMe (30% in MeOH, 2 mL) in anhydrous MeOH (75 mL) were stirred at room temperature overnight then concentrated under reduced pressure. The residue was partitioned between aqueous NH4Cl (25%) and hexanes. Organic layer was washed with brine, dried over anhydrous MgSO4, concentrated under reduced pressure. Flash chromatography purification (5%-20% EtOAc—hexanes gradient) gave methyl 5-((2-propylpentyl)oxy)furan-2-carboxylate as a colorless oil. Yield (0.38 g, 85%); 1H NMR (400 MHz, CDCl3) δ 7.12 (d, J=4.0 Hz, 1H), 5.27 (d, J=3.5 Hz, 1H), 3.99 (d, J=5.9 Hz, 2H), 3.03 (s, 3H), 1.74-1.83 (m, 1H), 1.20-1.40 (8H), 0.86-0.94 (m, 6H).

Provenance & Evidence