Methanol → HCID 10755930, compound

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Reaction Steps

The carboxylic acid thus obtained (610 mg, 2.2 mmol) was dissolved in 10 mL of methanol and 3 drops of con. H2SO4 was added. The resulting solution was heated to reflux for 20 hr, cooled to room temperature, and partitioned between sat. NaHCO3 and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure to an oil. Silica gel chromatography (4:1, hexanes:ethyl acetate) afforded (E)-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-2-methyl-prop-2-en-oate as a colorless solid (610 mg, 96%). 1H-NMR (300 MHz): d 2.15 (d, 3, J=1.2), 3.81 (s, 3), 3.88 (s, 3), 7.63 (s, 1). Anal. Calcd for C17H22O4 : C, 70.32; H, 7.64. Found: C, 70.44; H, 7.72.

Provenance & Evidence