Methanol → (Cyclopentyloxy)acetic acid

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).

1. additionwere added
2. temperatureThe mixture was heated
3. temperatureat reflux for 6 hours
4. concentrationThe mixture was concentrated under vacuum
5. additionthe residue was diluted with water (15 mL)
6. washwashed with hexanes (20 mL)
7. temperatureThe aqueous layer was cooled with ice
8. additionbrought to pH<3 by addition of 10% HCl (30 mL)
9. extractionThe resulting mixture was extracted with CH2Cl2 (3×20 mL)
10. extractionThe combined extract
11. concentrationwas concentrated under vacuum

ORD record

ord-fb414a3d52da4a9fb71df4e617546232

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609669B2