Methanol → (Cyclopentyloxy)acetic acid

Participants

Reaction Steps

The product from Example 133A (2.56 g) was combined with MeOH (10 mL) and 40% aqueous KOH (8 mL) and water (8 mL) were added. The mixture was heated at reflux for 6 hours, and then cooled to room temperature. The mixture was concentrated under vacuum, and the residue was diluted with water (15 mL) and washed with hexanes (20 mL). The aqueous layer was cooled with ice and brought to pH<3 by addition of 10% HCl (30 mL). The resulting mixture was extracted with CH2Cl2 (3×20 mL). The combined extract was concentrated under vacuum to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.52-1.83 (m, 8H) 4.05 (s, 2H) 4.06-4.12 (m, 1H).

Provenance & Evidence